Arthropodicidal fused tetrahydropyridazines

ABSTRACT

Arthropodicidal tetrahydropyridazines of Formulae I and II, ##STR1## wherein Q,X,X 1  Y, and G are as defined in the text, compositions containing them and their use in the control of arthropods.

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a continuation-in-part of application bearing U.S. Ser. No.07/570,103 filed on 17 Aug. 1990, now abandoned, which is acontinuation-in-part of application bearing U.S. Ser. No. 07/523,697filed on 15 May 1990, now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

Insecticidal tetrahydropyridazines, compositions containing them andmethods for controlling arthropods employing them.

2. State of the Art

Vaughan, J. Org. Chem., 20 (1955), pages 1619 to 1626, discloses1,5-diphenyl-2-pyrazoline-3-carboxamide.

U.S. Pat. No. 4,070,365 discloses insecticidal compounds of the formula:##STR2## wherein X is halogen; and Y is halogen, NO₂ or alkyl.

EP 153,127 discloses insecticidal compounds of the formula: ##STR3##wherein A is unsubstituted or substituted phenyl; B is unsubstituted orsubstituted phenyl; U is O, S or NR; and R, Y and Z are broadly defined.

Harhash et al., J. Heterocyclic Chem., 21 (1984), at page 1013,discloses the preparation of pyrazoline compounds: ##STR4## where R/Arare C₆ H₅ /C₆ H₅ ; CO₂ C₂ H₅ /C₆ H₅ ; C(O)NHC₆ H₅ /C₆ H₅ ; CH═CHC₆ H₅/C₆ H₅ ; and CH₃ /4-NO₂ -C₆ H₄.

J. Org. Chem., 1987, 52, 2277 discloses pyrazolidines as does Chem. Soc.Jap., 55, 2450 (1982).

EPA 330,678 EPA 322,168, WO 88/07994, WO 88/05046, WO 89/00562 and WO90/03378 disclose insecticidal pyrazolines.

SUMMARY OF THE INVENTION

The invention pertains to compounds of Formulae I and II, including allgeometric and stereoisomers, agriculturally suitable salts thereof,agricultural compositions containing them and their use for the controlof arthropods in both agronomic and nonagronomic uses. The compoundsare: ##STR5## wherein:

Q is selected from the group ##STR6##

A is H;

E is selected from the group H and C₁ -C₃ alkyl; or

A and E can be taken together to form V;

V is selected from the group --CH₂ --, --CH₂ CH₂ --, --O--, --S--,--SO--, --SO₂ --, --NR¹¹ --, --OCH₂ --, --SCH₂ --, --N(R¹¹)CH₂ --,substituted --CH₂ --, and substituted --CH₂ CH₂ --, the substituentsindependently selected from 1-2 halogen and 1-2 methyl; provided thatwhen V is --OCH₂ --, --SCH₂ -- or --N(R¹¹)CH₂ --, either atom can beattached to the aromatic moiety;

G is selected from the group ##STR7## X is selected from the group O, Sand N-X² ; X¹ is selected from the group Cl, Br, OR¹², SR¹² and NR¹² R¹³;

X² is selected from the group R¹², OH, OR¹², CN, SO₂ R¹², SO₂ Ph,OC(O)NR¹³ R¹⁴, OC(O)OR¹², NR¹³ R¹⁴ and phenyl optionally subtituted withR¹⁵ ;

Y is selected from the group H, C₁ -C₆ alkyl, benzyl optionallysubstituted by W, C₂ -C₆ alkoxyalkyl, CHO, C₂ -C₆ alkylcarbonyl, C₂ -C₆alkoxycarbonyl, C₂ -C₆ haloalkylcarbonyl, C₁ -C₆ alkylthio, C₁ -C₆haloalkylthio, phenylthio, R¹⁶ OC(O)NR¹⁷ S- and R¹⁸ (R¹⁹)NS-;

R¹ and R² are independently selected from the group H, C₁ -C₆ alkyl, C₁-C₆ haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃-C₆ haloalkynyl, C₂ -C₆ alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆nitroalkyl, C₂ -C₆ cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆cycloalkyl, C₃ -C₆ halocycloalkyl, phenyl optionally substituted with 1to 3 substituents independently selected from W, benzyl optionallysubstituted with 1 to 3 substituents independently selected from W,halogen, CN, N₃, SCN, NO₂, OR²¹, SR²¹, S(O)R²¹, S(O)₂ R²¹, OC(O)R²¹,OS(O)₂ R²¹, CO₂ R₂₁, C(O)R²¹, C(O)NR²¹ R²², SO₂ NR²¹ R²², NR²¹ R²², NR²²C(O)R²¹, OC(O)NHR.sup. 21, NR²² C(O)NHR²¹ and NR²² SO₂ R²¹ ; or when m,n or p is 2, (R¹)₂ when attached to adjacent atoms can be takentogether, or (R²)₂ when attached to adjacent atoms can be takentogether, or (R²⁰)₂ when attached to adjacent atoms can be takentogether as --OCH₂ O--, --OCF₂ O--, --OCH₂ CH₂ O--, --CH₂ C(CH₃)₂ O--,--CF₂ CF₂ O-- or --OCF₂ CF₂ O-- to form a cyclic bridge; provided thatwhen R¹, R² or R²⁰ is S(O)R²¹, S(O)₂ R²¹, OC(O)R²¹ or OS(O)₂ R²¹ thenR²¹ is other than H;

R³ is selected from the group H, J, N₃, NO₂, halogen, N(R²⁶)R²⁷, C₁ -C₆alkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₂ -C₆alkoxyalkyl, C₃ -C₈ alkoxycarbonylalkyl CO₂ R²¹, OR²³, C(O)R²¹, C(O)NR²¹R²², C(S)NR²¹ R²², C(S)R²¹, C(S)SR²¹, CN, Si(R³²)(R³³)R³¹, S(O)R³¹, SO₂R³¹, --P(O)(OR³¹)₂, phenyl, phenyl substituted by (R²⁰)_(p), benzyl andbenzyl substituted with 1 to 3 substituents independently selected fromW; or R³ is C₂ -C₆ epoxyalkyl optionally substituted with a groupselected from C₁ -C₃ alkyl, CN, C(O)R²⁸, CO₂ R²⁸ and phenyl optionallysubstituted with W; or R³ is C₁ -C₆ alkyl substituted with a groupselected from C(O)N(R²⁹)R³⁰, C(O)R²⁹, SR³¹, S(O)R³¹, SO₂ R³¹, SCN,halogen, CN, C₁ -C₂ haloalkoxy, Si(R³²)(R³³)R³¹, N(R²⁶)R²⁷, NO₂,OC(O)R²⁹ and J;

J is selected from the group consisting of saturated, partiallysaturated or aromatic 5- or 6- membered heterocyclic rings, bondedthrough carbon or nitrogen, containing 1-4 heteroatoms independentlyselected from the group consisting of 0-2 oxygen, 0-2 sulfur and 0-4nitrogen; said J value optionally containing one carbonyl and optionallysubstituted by one or more groups selected from W;

R⁴ is selected from the group H, halogen, C₁ -C₆ alkyl, CO₂ R²⁴, phenyl,pyridinyl and phenyl or pyridinyl substituted with Cl, Br, F, CF₃, NO₂,OCF₃, OCF₂ H or CN;

R⁵ and R⁷ are independently selected from the group H and C₁ -C₂ alkyl;

R⁶ is selected from the group H, C₁ -C₆ alkyl, CO₂ R²⁴, and optionallysubstituted phenyl and pyridinyl, wherein the substituents are selectedfrom Cl, Br, F, CF₃, NO₂, OCF₃, OCF₂ H or CN;

R⁴ and R⁵ can be taken together to form ═O;

R⁶ and R⁷ can be taken together to form ═O;

R⁸ is selected from the group H and C₁ -C₂ alkyl;

R⁹ is selected from the group H, C₁ -C₂ alkyl and C₁ -C₂ alkylcarbonyl;

R¹⁰ is selected from the group H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄alkylcarbonyl, C₂ -C₄ haloalkylcarbonyl, C₂ -C₄ alkoxycarbonyl C₂ -C₄haloalkoxycarbonyl, C₂ -C₅ alkylaminocarbonyl, C₃ -C₆ cycloalkyl, C₃ -C₆halocycloalkyl, C₄ -C₇ alkylcycloalkyl, C₄ -C₇ haloalkylcycloalkyl, C₁-C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl and SO₂ Ph optionallysubstituted with Cl, Br or CH₃ ;

R¹¹ is selected from the group H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄alkenyl, C₂ -C₄ haloalkenyl, SR²¹, S(O)R²¹, S(O)₂ R²¹, C(O)R²¹, CO₂ R²¹,C(O)NR²¹ R²⁵, C(S)NR²¹ R²⁵, C(S)R²¹, C(S)OR²¹, P(O)(OR²¹)₂, P(S)(OR²¹)₂,P(O)(R²¹)OR²¹, P(O)(R²¹)SR²⁵, and optionally substituted phenyl andbenzyl wherein the substituents(s) are selected from F, Cl, Br, CH₃, CF₃or OCF₃ ; provided that when R¹¹ is other than C(O)R²¹, C(O)NR²¹ R²⁵ orC(S)NR²¹ R²⁵ then R²¹ is other than H;

R¹² is selected from the group C₁ -C₃ alkyl, benzyl optionallysubstituted with R¹⁵, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, C₁ -C₃ haloalkyl,C₂ -C₄ haloalkenyl, C₃ -C₆ cycloalkyl and C₁ -C₃ alkyl substituted withOCH₃, OCH₂ CH₃, NO₂, CN, CO₂ CH₃, CO₂ CH₂ CH₃, SCH₃ or SCH₂ CH₃ ;

R¹³ is selected from the group H, C₁ -C₄ alkyl C₁ -C₄ haloalkyl, C₂ -C₄alkoxycarbonyl, and optionally substituted phenyl and pyridinyl whereinthe substituents(s) are selected from R₁₅ ; or

R¹² and R¹³ can be taken together to form --(CH₂)₄ --, --(CH₂)₅ -- or--CH₂ CH₂ OCH₂ CH₂ -- each of which is optionally substituted with 1 or2 CH₃ groups;

R¹⁴ is selected from the group H and C₁ -C₄ alkyl; or

R¹³ and R¹⁴ can be taken together to form --(CH₂)₄ --, --(CH₂)₅ -- orCH₂ CH₂ OCH₂ CH₂ each of which is optionally substituted with 1 or 2 CH₃groups;

R¹⁵ is selected from the group halogen, CN, C₁ -C₃ haloalkyl and C₁ -C₃haloalkoxy;

R¹⁶ is C₁ -C₆ alkyl;

R¹⁷ is C₁ -C₄ alkyl;

R¹⁸ and R¹⁹ are independently C₁ -C₄ alkyl; or

R¹⁸ and R¹⁹ can be taken together as --CH₂ CH₂ CH₂ CH₂ CH₂ -- or --CH₂CH₂ OCH₂ CH₂ --;

R²⁰ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃ -C₆ haloalkynyl, C₂ -C₆alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆ nitroalkyl, C₂ -C₆cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆ cycloalkyl, C₃ -C₆halocycloalkyl, phenyl optionally substituted with 1 to 3 substituentsindependently selected from W, benzyl optionally substituted with 1 to 3substituents independently selected from W, halogen CN, N₃, SCN, NO₂,OR²¹, SR²¹, S(O)R²¹, S(O)₂ R²¹, OC(O)R²¹, OS(O)₂ R²¹, CO₂ R²¹, C(O)R²¹,C(O)NR²¹ R²², SO₂ NR²¹ R²², NR²¹ R²², NR²² C(O)R²¹, OC(O)NHR²¹, NR²²C(O)NHR²¹ and NR²² SO R²¹ 2 ; or when m, n or p is 2, (R¹)₂ whenattached to adjacent atoms can be taken together, or (R²)₂ when attachedto adjacent atoms can be taken together, or (R²⁰)₂ when attached toadjacent atoms can be taken together as --OCH₂ O--, --OCF₂ O--, --OCH₂CH₂ O--, --CH₂ C(CH₃)₂ O--, --CF₂ CF₂ O-- or --OCF₂ CF₂ O-- to form acyclic bridge; provided that when R¹, R² or R²⁰ is S(O)R²¹, S(O)₂ R²¹,OC(O)R²¹ or OS(O)₂ R²¹ then R²¹ is other than H;

R²¹ is selected from the group H, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃ -C₆ haloalkynyl, C₂ -C₆alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆ nitroalkyl, C₂ -C₆cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆ cycloalkyl, C₃ -C₆halocycloalkyl, and optionally substituted phenyl and benzyl wherein thesubstituents are 1 to 3 substituents independently selected from W;

R²² is selected from the group H and C₁ -C₄ alkyl; or

R²¹ and R²² when attached to the same atom can be taken together as--(CH₂)₄ --, --(CH₂)₅ --, or --CH₂ CH₂ OCH₂ CH₂ --;

R²³ is selected from the group H, C₁ -C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄alkynyl, C₂ -C₄ alkylcarbonyl, C₂ -C₄ alkoxycarbonyl and C₁ -C₄alkylsulfonyl;

R²⁴ is C₁ -C₃ alkyl;

R²⁵ is selected from the group H, C₁ -C₄ alkyl, C₂ -C₄ alkenyl and C₂-C₄ alkynyl;

R²⁶ is selected from the group H, C(O)C₁ -C₆ alkyl, CO₂ C₁ -C₆ alkyl,optionally substituted C₁ -C₄ alkyl, optionally substituted C₂ -C₄alkenyl, and optionally substituted C₂ -C₄ alkynyl, the substituentsselected from C₁ -C₂ alkoxy, CN, C(O)R³⁴ and CO₂ R³¹ ;

R²⁷ is selected from the group H, C₁ -C₃ alkyl, phenyl, phenylsubstituted with W, benzyl and benzyl substituted with W;

R²⁸ is selected from the group H, C₁ -C₄ alkyl, C₂ -C₄ alkenyl and C₂-C₄ alkynyl;

R²⁹ and R³⁰ are independently selected from the group H and C₁ -C₂alkyl;

R³¹ is selected from the group C₁ -C₃ alkyl, phenyl and phenylsubstituted with W;

R³² is C₁ -C₃ alkyl;

R³³ is C₁ -C₃ alkyl;

R³⁴ is selected from the group H, C₁ -C₃ alkyl, phenyl and phenylsubstituted by W;

W is selected from the group halogen, CN, NO₂, C₁ -C₂ alkyl, C₁ -C₂haloalkyl, C₁ -C₂ alkoxy, C₁ -C₂ haloalkoxy, C₁ -C₂ alkylthio, C₁ -C₂haloalkylthio, C₁ -C₂ alkylsulfonyl and C₁ -C₂ haloalkylsulfonyl;

m is 1 to 3;

n is 1 to 3;

p is 1 to 3;

u is 1 or 2; and

Z is C or N.

Exemplary values of J include ##STR8##

Preferred Compounds A are those compounds of Formulae I and II wherein:

R¹ is selected from the group H, C₁ -C₆ alkyl, C₂ -C₆ haloalkyl, C₂ -C₆alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃ -C₆ haloalkynyl, C₂ -C₆alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆ nitroalkyl, C₂ -C₆cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆ cycloalkyl, C₃ -C₆halocycloalkyl, phenyl optionally substituted with 1 to 3 substituentsindependently selected from W, benzyl optionally substituted with 1 to 3substituents independently selected from W, halogen CN, SCN, NO₂, OR²¹,SR²¹, SO₂ R²¹, CO₂ R²¹, and C(O)R²¹, with one R¹ substituent in the4-position, or when m is 2 then (R¹)₂ when attached to adjacent atomscan be taken together as --CH₂ C(CH₃)₂ O--, --OCH₂ CH₂ O--, --OCF₂ CF₂O--, or --CF₂ CF₂ O-- to form a 5- or 6-membered fused ring;

R² is selected from the group H, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃ -C₆ haloalkynyl, C₂ -C₆alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆ nitroalkyl, C₂ -C₆cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆ cycloalkyl, C₃ -C₆halocycloalkyl, phenyl optionally substituted with 1 to 3 substituentsindependently selected from W, benzyl optionally substituted with 1 to 3substituents independently selected from W, halogen, CN, SCN, NO₂, OR²¹,SR²¹, S(O)₂ R²¹, OC(O)R²¹, OS(O)₂ R²¹, CO₂ R²¹, C(O)R²¹, C(O)NR²¹ R²²,SO₂ NR²¹ R²² and NR²¹ R²² ;

R³ is selected from the group H, C₁ -C₄ alkyl, C₃ -C₄alkoxycarbonylalkyl, CO₂ R²¹, C(O)R²¹, phenyl and phenyl substituted by(R²⁰)p;

R²⁰ is selected from the group halogen, C₁ -C₂ haloalkyl and CO₂ R²¹ ;

R²¹ is selected from the group C₁ -C₄ alkyl, C₁ -C₂ haloalkyl, C₃ -C₄alkenyl and propargyl;

R²² is selected from H and CH₃ ;

X¹ is selected from the group Cl, OR¹², SR¹² and N(CH₃)₂ ;

X² is selected from the group R¹², OR¹² and N(CH₃)₂ ;

m is 1 or 2;

n is 1 or 2; and

p is 1 or 2.

Preferred Compounds B are Compounds A wherein

G is selected from the group G-2, G-3, G-7 and G-9.

Preferred Compounds C are Compounds B where G is G-9.

Preferred Compounds D are Compounds C wherein

J is selected from the group J-1, J-2, J-8, J-9 and J-16.

Preferred Compounds E are Compounds D wherein

A and E are taken together to form --O--, --CH₂ --, --CH₂ CH₂ --, --OCH₂--, --S--, --SCH₂ -- N(R¹¹)CH₂ or NR¹¹ ;

R¹¹ is selected from the group H, C₁ -C₄ alkyl SO₂ R²¹, CO₂ R²¹ andCON(R²¹)R²⁵.

Preferred Compounds F are Compounds D wherein

A is H;

E is selected from the group H and C₁ -C₃ alkyl; and

R² is in the 3-position

Preferred Compounds G are Compounds E of Formula wherein Q is Q-1.

Preferred Compounds H are Compounds E of Formula I wherein Q is Q-2.

Preferred Compounds I are Compounds E of Formula II wherein Q is Q-1.

Preferred Compounds J are Compounds E of Formula II wherein Q is Q-2.

Preferred Compounds K are Compounds F of Formula I wherein Q is Q-1.

Preferred Compounds L are Compounds F of Formula I wherein Q is Q-2.

Preferred Compounds M are Compounds F of Formula II wherein Q is Q-1.

Preferred Compounds N are Compounds F of Formula II wherein Q is Q-2.

In the above recitations, the term "alkyl", used either alone or incompounds words such as "alkylthio" or "haloalkyl", denotes straightchain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or thedifferent butyl, pentyl, hexyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and thedifferent butoxy, pentoxy or hexyloxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g., vinyl,1-propenyl, 2-propenyl, 3-propenyl and the different butenyl, pentenyland hexenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl,1-propynyl, 3-propynyl and the different butynyl, pentynyl and hexynylisomers.

Alkylthio denotes methylthio, ethylthio and the different propylthio,butylthio, pentylthio and hexylthio isomers.

Alkylsulfinyl, alkylsulfonyl, alkylamino, etc., are defined analogouslyto the above examples.

Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in compound words such as"haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as "haloalkyl" said alkyl may bepartially or fully substituted with halogen atoms, which may be the sameor different. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂CHFCl. The terms "halocycloalkyl", "haloalkenyl" and "haloalkynyl" aredefined analogously to the term "haloalkyl".

The total number of carbon atoms in a substituent group is indicated bythe "C_(i) -C_(j) " prefix where i and j are numbers from 1 to 8. Forexample, C₁ -C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl; C₂ alkoxyalkoxy designates OCH₂ OCH₃ ; C₄ alkoxyalkoxydesignates the various isomers of an alkoxy group substituted with asecond alkoxy group containing a total of 4 carbon atoms, examplesincluding OCH₂ OCH₂ CH₂ CH₃ and OCH₂ CH₂ OCH₂ CH_(3;) C₂ cyanoalkyldesignates CH₂ CN and C₃ cyanoalkyl designates CH₂ CH₂ CN and CH(CN)CH₃; C₂ alkylcarbonyl designates C(O)CH₃ and C₄ alkylcarbonyl includesC(O)CH₂ CH₂ CH₃ and C(O)CH(CH₃)₂ ; and as a final example, C₃alkoxycarbonylalkyl designates CH₂ CO₂ CH₃ and C₄ alkoxycarbonylalkylincludes CH₂ CH₂ CO₂ CH₃, CH₂ CO₂ CH₂ CH₃ and CH(CH₃)CO₂ CH₃.

DETAILS OF THE INVENTION

Compounds of Formulae I and II are prepared as described in Schemes 1through 27 with substituents as previously defined, unless otherwisenoted. The substituents R⁴, R⁵, R⁶ and R⁷ have been depicted as hydrogenfor the purposes of clarity but also included are the values of thesesubstituents as previously defined.

Compounds of Formula II (Q-1) can be prepared by the reaction ofimidoylhalides of Formula II (Q-1) with sulfur, oxygen and nitrogennucleophiles of Formula III as illustrated in Scheme 1. Typicalreactions involve the combination of equimolar amounts of II (Q-1) andIII in the presence of a base such as an alkali metal, tertiary amine,metal hydride and the like in conventional organic solvents, includingether, tetrahydrofuran 1,2-dimethoxyethane, methylene chloride,chloroform, N,N-dimethylformamide and dimethylsulfoxide. The reactioncan be conducted at temperatures ranging from -20° C. to 100° C. withtemperatures in the range of -10° C. to 30° C. generally beingpreferred. One skilled in the art will recognize that reactions of thisgeneral type can be extended to other nucleophilic reagents. ##STR9##

The imidoylhalides of Formula II (Q-1) can be prepared by the reactionof Formula I (Q-1) compounds with an appropriate halogenating agent suchas phosphorous trichloride, phosphorous pentachloride, phosphoroustribromide, phosphorous pentabromide, thionyl chloride, sulfurylchloride, triphenyl phosphine and carbon tetrachloride (Wolkoff, Can. J.Chem., 1975, 53, 1333) and the like (see Fieser and Fieser, Reagents forOrganic Synthesis, Vol. I, 1967) as illustrated in Scheme 2. Typicalreactions involve the combination of Formula I (Q-1) compounds with anexcess of the halogenating agent ranging from 1.1 to 10 equivalents,with 2 to 4 equivalents being preferred. The reaction can be conductedin the absence of a solvent or in the presence of a conventional organicsolvent such as benzene, toluene, xylene, chloroform, methylenechloride, hexane and the like. The reaction temperature can range from-10° C. to 200° C. with 35° C. to 100° C. being perferred.

The reaction is generally complete after 24 hours. ##STR10##

Alternatively, compounds of Formula II (Q-1), when X¹ is equal to R¹²--S, can be prepared by the reaction of compounds of the Formula I (Q-1)where X is equal to S with an electrophile of the Formula IV in thepresence of a suitable base, as illustrated in Scheme 3. Typicalreactions involve the combination of equimolar amounts of Formula I(Q-1) compounds and the appropriate electrophile of Formula IV. A basesuch as an alkali metal, tertiary amine or metal hydride can be used.##STR11##

Compounds of Formula I (Q-1) where X is S or O can be prepared by thereaction of Formula V compounds with isocyanates of Formula VI. Typicalreactions involve the combination of equimolar amounts of V and VI in aconventional organic solvent such as but not limited to ethyl acetate,methylene chloride, chloroform, benzene or toluene. A base such as analkali metal, tertiary amine or metal hydride can be used. Scheme 4illustrates this transformation. ##STR12##

The preparation of Formula V compounds can be accomplished by thereaction of Formula VII compounds with a reducing agent such as LiAlH₄or BH₃ (see J. Org. Chem., 1973, 38, 912). The typical reaction involvesthe combination of an excess in molar amounts of the reducing agent (1.1equivalents to 5.0 equivalents) with 1 equivalent of a Formula VIIcompound. Conventional aprotic organic solvents such as diethyl ether,tetrahydrofuran or 1,2-dimethoxyethane can be used. The reactiontemperature can vary from 0° C. to the reflux temperature of theparticular solvent being used and the reaction is usually complete inless than 24 hours. Scheme 5 illustrates this transformation. ##STR13##

The preparation of Formula VII compounds can be accomplished by thereaction of Formula VIII compounds with an excess of equivalents (1.1 to10.0 equivalents) of hydrazine, hydrazine monohydrate, hydrazineacetate, hydrazine hydrochloride and the like. The reaction is conductedin an alcohol solvent such as methanol, ethanol, n-propanol,isopropanol, n-butanol and the like or acetic acid and the temperatureis governed by the reflux temperature of the particular solvent. Thereaction is generally complete in 24 hours. Scheme 6 illustrates thistransformation. Alternatively, Formula V compounds can be prepared fromFormula VIIIa derivatives as described for the preparation of FormulaVII compounds (Scheme 6). ##STR14##

Compounds of Formula VIII where R³ is equal to H can be prepared by thereduction of Formula IX compounds. This transformation can be effectedby catalytic hydrogenation (House, Modern Synthetic Reactions, 1972, pp.1-44) or more conveniently through the use of an excess of equivalents(1.5 to 4.0 equivalents) of zinc in refluxing acetic acid as solvent (J.Med. Chem., 1986, 29, 2181). The reaction is usually complete in 24hours. Scheme 7 illustrates this transformation. ##STR15##

Compounds of Formula IX can be prepared by the reaction of Formula Xderivatives with Formula XI compounds. One skilled in the art willrecognize this reaction as an Aldol condensation (House, ModernSynthetic Reactions, 1972, pp. 629-733) which is a well knowntransformation; see Scheme 8. ##STR16##

The starting ketones of Formula X are known in the art or can beobtained by methods analogous to known procedures. Those skilled in theart will recognize the Formula X compounds to include, indanones,tetralones, chromanones, thiochromanones, benzofuran-3-ones,isochromanones and others.

Alternatively, compounds of Formula VIII can be prepared by hydrolysisof Formula XII compounds. One skilled in the art will recognize thistransformation as conventional and well understood. Scheme 9 illustratesthis common reaction. ##STR17##

Formula XII compounds can be prepared by the alkylation of Formula XIIIderivatives with Formula XIV compounds. The reaction can be accomplishedby the reaction of equimolar amounts of Formula XIII and XIV compoundsin the presence of a base such as an alkali metal, tertiary amine, metalhydride and the like in a conventional organic solvent such as, but notlimited to, ether, tetrahydrofuran, 1,2-dimethoxyethane,dimethylformamide, dimethylsulfoxide, methanol, ethanol and propanol.The reaction is usually conducted at temperatures between 0° C. and thereflux temperature of the solvent utilized. The reaction is usuallycomplete in 48 hours. Scheme 10 (reaction A) illustrates thistransformation.

Additionally, the ketone XIII serves as a useful intermediate forcompounds of Formula VIIIa. Formula VIIIa compounds can be prepared bythe alkylation of Formula XIII derivatives with Formula XIVa compounds.The reaction can be accomplished by the reaction of one equivalent ofFormula XIII compounds and one to ten equivalents of Formula XIVacompounds in the presence of a base such as an alkali metal, tertiaryamine, metal hydride and the like in a conventional organic solvent suchas, but not limited to, ether, tetrahydrofuran, 1,2-dimethoxyethane,dimethylformamide, dimethylsulfoxide, methanol, ethanol and propanol.The reaction is usually conducted at temperatures between 0° C. and thereflux temperature of the solvent utilized. The reaction is usuallycomplete in 48 hours. Scheme 10 (reaction B) illustrates thistransformation. ##STR18##

The starting ketones of Formula XIII are known in the art or can beobtained by methods analogous to known procedures.

Compounds of Formula II (Q-2) can be prepared from Formula II (Q-2)imidoylhalide derivatives in an analogous fashion such as that describedfor the preparation of Formula II (Q-1) imidoylhalide compounds; seeScheme 11. ##STR19##

Formula II (Q-2) imidoylhalide compounds can be prepared from Formula I(Q-2) compounds in an analogous fashion as that described for Formula II(Q-1) compounds; see Scheme 12. ##STR20##

Compounds of Formula I (Q-2) can be prepared by the reaction of the acidchloride XV with a substituted aniline of Formula XVI in equimolarproportions in the presence of an excess of an acid scavenger, such astertiary alkylamines or pyridines, but not limited to these, in anaprotic organic solvent such as ether, tetrahydrofuran, chloroform,methylene chloride, benzene and/or toluene. Scheme 13 illustrates thistransformation. ##STR21##

Compounds of the Formula XV can be prepared from compounds of theFormula XVII through conventional methodology generally used for theconversion of esters to their corresponding acid chlorides asillustrated in Scheme 14. ##STR22##

Formula XVII derivatives (when A and E are taken together to form V) canbe prepared from Formula XVIII compounds by the reaction of FormulaXVIII compounds with a base such as, but not limited to, sodium hydride,potassium hydride, sodium carbonate, potassium carbonate, sodiummethoxide and lithium diisopropylamide. Suitable solvents include, butare not limited to, methylene chloride, chloroform, tetrahydrofuran,ether and toluene. The reaction temperature can range from 0° C. to thereflux temperature of the particular solvent utilized and the reactionis generally complete in 24 hours. Literature precedent for thisdiazoalkene Dieis-Alder reaction is found in J. Chem. Soc.. P.T.I.,1987, 2517. Scheme 15 demonstrates the methodology used to accomplishthe transformation described above. ##STR23##

Compounds of Formula XVIII can be prepared from compounds of the FormulaXIX by the reaction with an equimolar amount of XX in conventionalorganic solvents such as, but not limited to, ether, tetrahydrofuran,methanol, ethanol, methylene chloride, benzene and toluene. Typicalreaction temperatures can range from room temperature to the refluxtemperature of the particular solvent utilized and the reaction isusually complete in 24 hours. Scheme 16 illustrates this reaction.##STR24##

Formula XIX compounds can be prepared from Formula XXI derivatives by adiazatization/reduction reaction well documented in the literature (seeOrganic Functional Group Preparation, 1983, pp. 452-453 and referencescited therein). Scheme 17 illustrates this transformation. ##STR25##

Formula XXI compounds are known in the art or can be obtained by methodsanalogous to known procedures. Those skilled in the art will recognizeFormula XXI compounds to be substituted anilines or aminopyridines.

Compounds of Formulae I (Q-3) and II (Q-3) can be prepared by thereaction of Formulae I (Q-1) and II (Q-1) derivatives with an oxidizingagent, such as dichlorodicyanobenzoquinone (DDQ) (see Fieser and Fieser,Reagents for Organic Synthesis, 1967, Vol. I, pp. 215-219). The reactioninvolves the combination of an excess of molar equivalents of DDQ withone molar equivalent of Formula I (Q-1) or Formula II (Q-1) compounds ina suitable solvent such as, but not limited to, methanol, ethanol,acetone and benzene. The reaction is conducted at room temperature tothe reflux temperature of the particular solvent utilized. The reactionis usually complete in 24 hours. Scheme 18 illustrates this reaction.##STR26##

Compounds of Formulae I (Q-4) and II (Q-4) can be prepared from FormulaI (Q-2) and II (Q-2) derivatives in an analogous fashion such as thatdescribed for Formulae I (Q-3) and II (Q-3) compounds; see Scheme 19.##STR27##

Compounds of Formula I (Q-5) can be prepared by the reaction of tri- andtetravalent metal species such as titanium, silicon, tin and the like incombination with reducing agents such as sodium, lithium, or zincborohydride, lithium aluminum hydride and the like with compounds ofFormula I (Q-1) as illustrated in Scheme 20. Literature precedent foranalogous reactions can be found in J. Org. Chem., 1987, 54, 3750, andSynthesis, 1980, 695. Typical reactions involve the addition of 1equivalent of a compound of Formula I (Q-1) to a solution of 1.1 to 4.0equivalents of titanium tetrachloride, with 1.5 to 2.5 equivalents beingpreferred, and 2.1 to 6.0 equivalents of sodium borohydride with 3.5 to4.5 equivalents being preferred.

Conventional organic solvents such as ether, tetrahydrofuran,dimethoxyethane, methylene chloride and chloroform can be used with1,2-dimethoxyethane being preferred. The reaction can be conducted attemperatures ranging from -70° C. to 50° C. with -10° C. to 30° C. beingpreferred. The reaction time can be 0.1 hour to 48 hours with 2 to 4hours being preferred. ##STR28##

Formula I (Q-5) derivatives can be converted into Formula II (Q-5)compounds in an analogous fashion as described for the conversion ofFormula I (Q-1) compounds into Formula II (Q-1) derivatives.

Formulae I (Q-6) and II (Q-6) compounds can be prepared in an analogousfashion as described for the preparation of Formulae I (Q-5) and II(Q-5) derivatives.

Additionally, compounds of Formula I, where Q is Q-1, A is H, Z is CH, Eis H and R³ is H alkyl or aryl, can be prepared as outlined in Scheme21. This is generally accomplished by the reaction of equimolar amountsof a pyridazine such as XXII with an aryl isocyanate or isothiocyanateof Formula VI in conventional organic solvents such as ether ortetrahydrofuran. The Formula I compounds of Scheme 21, where E is H, canbe converted to the analogs where E is C₁ -C₃ alkyl by alkylation of thedianion with a C₁ -C₃ alkyl halide as shown. This is typically done bytreatment of the compound where E is H with at least two equivalents ofa strong base such as lithium diisopropylamide at low temperatures inthe range of 0° to -78° C. in a solvent such as tetrahydrofuran. Analkyl halide (typically the iodide) is then added to the preformeddianion affording, after workup, compounds of Formula I where Q is Q-1,A is H and E is C₁ -C₃ alkyl. ##STR29##

Alkylation of the dianion of compounds such as XXIII is another usefulmethod for the introduction of a variety of R³ groups, this method isoutlined in Scheme 22. The R³ groups generalily prepared by this methodare derived from alkylating reagents R³ -L (where L is Cl, or I) andinclude e.g. alkyl halides, substituted alkyl halides, acyl halides,alkylchloroformates, sulfenyl and sulfonyl halides, dialkylcarbamoylhalides and the like. Typical procedures are analogous to that describedin Scheme 21 and include the use, of strong base at low temperature. Asecond substituent E (where E is C₁ -C₃ alkyl), can also be introducedin a similar fashion. ##STR30##

Compounds of Formula I, where Q is Q-1 and R⁶ and R⁷ are taken togetherto form a carbonyl group (such as compound XXV) can be prepared by thereaction of an amide such as XXIV with an aryl isocyanate orisothiocyanate. This method is outlined in Scheme 23. This reaction canbe run in a variety of conventional organic solvents such as ether,tetrahydrofuran or ethyl acetate and is preferably conducted at thereflux temperature of the solvent. It is also preferable, and in somecases necessary, to add a catalytic amount of an amine base such astriethylamine, pyridine or preferably dimethylaminopyridine. ##STR31##

Intermediate pyridazines, such as XXIII, are generally available inthree steps as shown in Scheme 24. Friedel-Crafts acylation of asubstituted benzene (where R² is generally an ortho/para directinggroup) with 4-chlorobutyryl chloride affords the 4-chlorobutyrophenoneXXVI. Treatment of XXVI with hydrazine in refluxing alcoholic solventssuch as methanol or ethanol followed by reaction with an aryl isocyanateas in Scheme 21 affords the pyridazines XXIII, each of these reactionsis well documented in the chemical literature. ##STR32##

Intermediate pyridazines, such as XXII, where R³ is H, alkyl or aryl canbe prepared by the reduction of pyridazinones, such as XXVII, withreducing agents such as lithium aluminum hydride or borane intetrahydrofuran as outlined in Scheme 25. Both of these reductivemethods are documented in the chemical literature and are also describedin more detail in Scheme 5. ##STR33##

Intermediate pyridazinones of Formula XXVII can be prepared in threesteps from substituted acetophenones or deoxybenzoins (R³ is H, alkyl orphenyl) of Formula XXVIII as shown in Scheme 26. Alkylation of XXVIIIwith, e.g., ethyl bromoacetate under typical alkylation conditions suchas sodium hydride in tetrahyrofuran or dimethylformamide followed bybasic hydrolysis of the ester and subsequent acidification affords theintermediate acid XXIX. Treatment of XXIX with hydrazine in refluxingalcoholic solvents such as ethanol or isopropanol affords thepyridazinones of Formula XXVII. ##STR34##

Compounds of Formula I, where Q is Q-1 and G is an aromatic heterocycle,can be prepared by treating intermediates of Formula V (as thehydrochloric acid addition salt) with triphosgene (O=C(OCCl₃)₂) and NH₂-G in the presence of a base such as pyridine as outlined in Scheme 27.##STR35##

In a manner similar to that described for compounds where Q is Q-1 and Ais H the application of the chemistry described in Schemes 11 through 20can be used to prepare compounds where A is H for the Q values Q-2, Q-3,Q-4, Q-5, and Q-6.

Formula I compounds, where Y is other than H, can be prepared bystandard alkylation, acylation or sulfenylation methods well documentedin the literature.

It is recognized that in many of the transformations described it willbe necessary to utilize appropriate protecting groups to preventunwanted side reactions or use reagents that do not affect functionalityother than that desired. One skilled in the art will be able to selectappropriate protecting groups and reagents to this end.

The following Examples further illustrate the invention.

EXAMPLE 1 Step A: (2,3,-Dihydro-1-oxo-1H-indenylidene)acetic acid

To a solution of 1.3 mL of H₂ SO₄ dissolved in 75 mL H₂ O was added 11.3g (0.053 mol) of sodium periodate. The reaction mixture was cooled to 0°C. and 8.0 g (0.053 mol) of tartaric acid was added all at once andstirred for 15 min. at room temperature. 5.0 g (0.038 mol) of 1-indanonewas added all at once followed by the dropwise addition of 19.0 g (0.24mol) of 50% NaOH dissolved in 40 mL of H₂ O. A white precipitate wasformed and 75 mL of ethanol was added. The reaction mixture was stirredat room temperature for 1 hour, acidified to pH ˜2 with concentrated HCland stirred for 18 hours at room temperature, filtered and dried toafford 3.3 g of a yellow solid. ¹ H NMR (CDCl₃) δ: 4.08 (s, 2H), 6.54(s, 1H), 7.4-7.8 (m, 5H).

Step B: 2,3-Dihydro-1-oxo-1H-indene-2-acetic acid

To a solution of 1.9 g (0.031 mol) of zinc dust suspended in 10 mL ofHOAc was added 2.3 g (0.012 mol) of the product from Step A. Thereaction mixture was refluxed for 1 hour, cooled, filtered and rinsedwtih acetic acid. The acetic acid solution was poured into 200 mL of H₂O and extracted with ethyl acetate (3 ×50 mL), washed with H₂ O (2×50mL), dried over anhydrous magensium sulfate, filtered and concentratedunder vacuum to afford 1.9 g of a yellow solid. ¹ H NMR (CDCl₃) δ:2.6-3.5 (m, 5H), 7.4-7.8 (m, 4H), 12.2 (s, 1H).

Step C: 2,4,4a,5-Tetrahydro-3H-indeno[1,2-c]-pyrodazin-3-one

To a solution of 0.53 g (0.011 mol) of hydrazine hydrate dissolved in 25mL ethanol was added 1.2 g (0.0089 mol) of the product from step B. Thereaction mixture was refluxed for 18 hours, cooled to room temperature,concentrated under vacuum, added 100 mL H₂ O and extracted with ethylacetate (3×50 mL), washed wtih brine (1×100 mL), dried over anhydrousmagnesium sulfate, filtered and concentrated under vacuum to afford 1.0g of a yellow solid. ¹ H NMR (CDCl₃) δ: 2.36 (t, 1H), 2.78 (dd, 1H),2.90 (dd, 1H), 3.20 (m, 1H), 3.41 (dd, 1H), 7.35 (m, 3H), 7.75 (d, 1H),8.45 (s, 1H). IR (mineral oil): 3213, 1702 cm⁻¹.

Step D:3,4,4a,5-Tetrahydro-N-[4-(trifluoromethyl)-phenyl]-2H-indeno[1,2-c]pyridazin-2-carboxamide

To a solution of 0.204 g (0.0053 mol) of lithium aluminum hydridesuspended in 20 mL THF was added dropwise 1.0 g (0.0053 mol) of theproduct from step C dissolved in 10 mL THF. The dark reaction mixturewas refluxed for 1 hour, cooled to 0° C. and 50 mL of a saturatedsolution of ammonium chloride was added. The reaction was extracted withethyl acetate (3×50 mL), washed with brine (1×100 mL), dried overanhydrous magnesium sulfate, filtered into a flask and added 1.0 g(0.0053 mol) α,α,α-trifluoro-p-tolylisocyanate all at once. The reactionwas stirred for 0.5 hours, concentrated under vacuum and chromatographedusing 30% ethyl acetate/70% hexanes as eluent to afford 0.250 g of apurple solid, mp 136-138° C. ¹ H NMR (CDCl₃) δ: 1.71 (ddd, 1H), 2.45 (m,1H), 2.79 (dd, 1H), 2.95 (m, 1H), 3.35 (dd, 1H), 3.38 (dt, 1H), 4.58(ddd, 1H), 7.32-7.4 (m, 3H), 7.57 (d, 2H), 7.69 (d, 2H), 7.70 (d, 1H),8.83 (s, 1H). IR (mineral oil): 3362, 1679 cm⁻¹.

EXAMPLE 2 Step A: 3-Fluoro-α-(4-fluorophenyl)-benzenepropanoic acid

To a solution of 10.8 g of 60% sodium hydride in 400 mL oftetrahydrofuran was added 44.7 g of methyl 4-fluorophenylacetatedropwise. Then, 50 g of 3-fluorobenzyl bromide was added dropwise. Themixture was then heated to reflux for approximately 18 hours. After thistime, the reaction was cooled to room temperature and filtered. Thefiltrate was partitioned between ether and 5% aqueous sodiumbicarbonate, and the ether extracts were dried over magnesium sulfateand concentrated to 77.57 g of a yellow oil. The crude product wascombined with 275 mL of methanol, 20 mL of 50% aqueous NaOH and 50 mL ofH₂ O and the mixture was refluxed for about 18 hours. The reaction wasthen cooled to room temperature, concentrated and partitioned betweenwater and ether. The aqueous extracts were made acidic with concentratedHCl and extracted with ether. The ether extracts were dried over MgSO₄,filtered, concentrated and the crude product was triturated with hexaneto afford 43.62 g of a white solid; mp 92-94° C. ¹ H NMR (CDCl₃) δ: 3.00(dd, 1H), 3.38 (dd, 1H), 3.83 (t, 1H), 6.8-7.4 (m, 6H).

Step B: 5-Fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one

A solution of 500 g of polyphosphoric acid was heated to 60° C. and 43.0g of the acid from step A was added. The mixture was then heated to 110°C. for 1 hour. After this time, the reaction was cooled to about 60° C.and 400 mL of water was added rapidly with externalcooling. The mixturewas then partitioned between toluene and water, washed twice withtoluene and the combined toluene extracts were then washed with 5%aqueous NaHCO₃. The toluene extracts were then dried over MgSO₄,filtered, concentrated and chromatographed on silica gel with 10% ethylacetate in hexane as the eluent to afford, after trituration withhexane, 26.98 g of a yellow solid; mp 72°-74° C. ¹ H NMR (CDCl₃) δ: 3.22(dd, 1H), 3.70 (dd, 1H), 3.94 (dd, 1H), 7.0-7.3 (m, 5H), 7.82 (dd, 1H).

Step C: Ethyl5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1-oxo-1H-indene-2-acetate

To a solution of 0.720 g (0.018 mol) of 60% sodium hydride suspended in50 mL DMF at 10° C. was added dropwise 4.0 g (0.0164 mol) of the productfrom step B dissolved in 25 mL DMF. The reaction mixture was stirred at10° C. for 20 min. and 3.1 g (0.0164 mol) ethyl bromoacetate was addedall at once. The reaction was heated at 60° C. for 15 min, cooled toroom temperature, poured into 200 mL 10% HCl, extracted with ethylacetate (3×50 mL), washed with brine (1×100 mL), dried over anhydrousmagnesium sulfate, filtered and concentrated under vacuum to afford 4.0g of a viscous oil. ¹ H NMR (CDCl₃) δ: 1.10 (t, 3H), 3.18 (s, 2H), 3.63(s, 2H), 4.18 (q, 2H), 6.95-7.30 (m, 6H), 7.80 (dd, 1H). IR (neat):1720, 1676 cm⁻¹ .

Step D: 5-Fluoro-2-(4-fluorophenyl)-2-3-dihydro-1-oxo-1H-indene-2-aceticacid

To a solution of 100 mL of 1N sodium hydroxide dissolved in 100 mL ofCH₃ OH was added 4.0 g of the product obtained from step C. The reactionmixture was refluxed for 45 min., cooled to room temperature, pouredinto 200 mL H₂ O, extracted with ethyl acetate (3×50 mL), acidified theaqueous phase with 1N HCl, and extracted with ethyl acetate (3×50 mL),washed with brine (1×100 mL), dried over anhydrous magnesium sulfate,filtered and concentrated under vacuum to afford 3.1 g of a yellowsolid. ¹ H NMR (Me₂ SO-d₆) δ: 3,14 (d, 2H), 3.61 (d, 2H), 7.02-7.40 (m,5H), 7.50 (dd, 1H), 7.78 (dd, 1H). IR (mineral oil): 3300-2600, 1739,1677 cm⁻¹.

Step E: 7-Fluoro-4a-(4-fluorophenyl)-2,4,4a,5-tetrahydro-3H-indeno[1,2-c]pyridazin-3-one

3.1 g (0.010 mol) of the product from step D was subjected to the sameprocedure as described in Example 1, step C, to afford 2.0 g of a yellowsolid. ¹ H NMR (CDCl₃) δ: 2.83 (d, 2H), 3.30 (d, 2H), 6.95-7.20 (m, 6H),7.80 (dd, 1H), 8.48 (s, 1H).

Step F: 7-Fluoro-4a-(4-fluorophenyl)-3,4,4a,5-tetra-hydro-N-[4-(trifluoromethyl)phenyl]-2H-indeno[1,2-c]-pyridazine-2-carboxamide

2.0 g (0.007 mol) of the product from step E was subjected to the sameprocedure as described in Example 1, step D, to afford 0.10 g of a whitesolid: mp 224-227° C. ¹ H NMR (CDCl₃) δ: 2.07 (dt, 1H), 2.60 (ddd, 1H),2.85 (dt, 1H), 3.32 (d, 1H), 3.44 (d, 1H), 4.33 (ddd, 1H), 6.9-7.2 (m,6H), 7.58 (d, 2H), 7.68 (d, 2H), 7.75 (dd, 1H), 8.82 (s, 1H). IR(mineral oil): 3328, 1667 cm⁻¹.

EXAMPLE 3 Step A: (1,2,3,4-Tetrahydro-1-oxo-2-naphthalenylidene)-aceticacid

10.0 g (0.068 mol) of 1-tetralone was subjected to the same procedure asdescribed in Example 1, step A, to afford 2.8 g of an orange solid. ¹ HNMR (CDCl₃) δ: 3.0 (m, 2H), 3.32 (m, 2H), 6.69 (s, 1H), 7.40 (m, 2H),7.6 (t, 1H), 7.98 (d, 1H).

Step B: 1,2,3,4-Tetrahydro-1-oxo-2-naphthalene-acetic acid

2.80 g (0.014 mol) of the product from step A was subjected to the sameprocedure as described in Example 1, step B, to afford 2.0 g of aviscous oil. ¹ H NMR (CDCl₃) δ: 2.0 (m, 1H), 2.25 (m, 1H), 2.50 (m, 1H),3.0 (m, 4H), 7.28 (m, 2H), 7.45 (t, 1H), 8.0 (d, 1H), 11.2 (s, 1H).

Step C: 2,4,4a,5-Tetrahydro-3H-indeno[1,2-c]-pyridazin-3-one

2.0 g (0.0098 mol) of the product from step B was subjected to the sameprocedure (n-butanol was substituted for ethanol as the solvent) asdescribed in Example 1, step 3, to afford 1.0 g of an orange solid. ¹ HNMR (CDCl₃) δ: 1.62 (m, 1H), 2.2 (m, 2H), 2.6-3.0 (m, 4H), 7.1-7.4 (m,3H), 8.04 (d, 1H), 8.59 (s, 1H).

Step D:3,4,4a,5-Tetrahydro-N-[4-(trifluoromethyl)-phenyl]-2H-indeno[1,2-c]pyridazine-2-carboxamide

1.0 g (0.0046 mol) of the product from step C was subjected to the sameprocedure as described in Example 1, step D, to afford 1.0 g of a whitesolid; mp 122° C.-124° C. ¹ H NMR (CDCl₃) δ: 1.6 (m 2H), 2.2 (m,2H),2.45 (m. 2H), 1H), 2.95 (m, 2H), 3.28 (dt, 1H), 4.64 ddd, 1H), 7.18(m, 1H), 7.3 (m, 2H), 7.57 (d, 2H), 7.79 (d, 2H), 8.05 (m, 1H), 8.92 (s,1H). IR (mineral oil): 3375, 1697 cm⁻¹.

EXAMPLE 4 Step A: 3-Phenyl-4-oxo-benzenebutanoic acid

To a solution of 6.0 g of 60% sodium hydride in 150 ml of THF was addeddropwise a solution of 29.4 g of deoxybenzoin in 150 ml THF. The mixturewas stirred for 10 min., 16.8 ml of ethylbromoacetate was addeddropwise, and the reaction was then heated at reflux under nitrogenovernight. The reaction was then partitioned between ether and 5%aqueous sodium bicarbonate, washed twice with ether dried over magnesiumsulfate, filtered and concentrated to 41.08 g of a brown oil. The crudeproduct was mixed with 200 ml of methanol, 30 ml of water and 10 ml of50% sodium hydroxide and then heated to reflux under nitrogen overnight.After this time the reaction was concentrated, partitioned between waterand ether, washed twice with ether and dried over magnesium sulfate. Theether extracts were then concentrated and the residue triturated withcold ether to afford 6.45 gms of a yellow solid, mp 137-139° C. ¹ H NMR(CDCl₃) δ: 2.74 (dd, 1H), 3.43 (dd, 1H), 5.04 (dd, 1H), 7.1-7.5 (m, 8H),7.93 (d, 2H).

Step B: 4,5-dihydro-5,6-diphenyl-3(2H)-pyridazinone

To a mixture of 3.0 gms of the product from Step A in 25 ml of isopropylalcohol was added 1.0 ml of hydrazine hydrate and the mixture wasrefluxed under nitrogen overnight. The reaction was then cooled to 0° C.and filtered and the solids were washed with water and then coldisopropyl alcohol. This afforded 2.32 g of a white solid, mp 221°-223°C. ¹ H NMR (CDCl₃) δ: 2.80 (d, 1H), 3.05 (dd, 1H), 4.50 (d, 1H), 7.1-7.5(m, 8H), 7.69 (m, 2H), 8.76 (bs, 1H).

Step C: 5,6-Dihydro-6-oxo-3,4-diphenyl-N-[4-(trifluoromethyl)phenyl]-1(4H)-pyridazinecarboxamide

To a mixture of 0.27 g of the product from Step B and 0.19 g of4-trifluoromethyl isocyanate in 2 ml of THF was added 50 mg ofdimethylaminopyridine and the mixture was heated under nitrogen for 4hrs. The mixture was then concentrated and chromatographed on silica gelto afford 0.10 g of a yellow solid; mp 164-166° C. ¹ H NMR (CDCl₃) δ:3.04 (dd, 1H), 3.23 (dd, 1H), 4.52 (bd, 1H), 7.1-7.5 (m, 8H), 7.60 (d,2H), 7.73 (d, 2H), 7.88 (d, 2H), 10.95 (bs, 1H).

EXAMPLE 5 Step A: 5,6-Dihydro-3,4-diphenyl-N-[4-(trifluoromethyl)phenyl]-1(4H)-pyridazine carboxamide

To a mixture of 1.1 g of the product from Example 4, Step B in 10 ml ofTHF was added slowly 4.0 ml of 1.0 M lithium aluminum hydride in THF, a10° C. exotherm was observed. The reaction was then stirred undernitrogen at ambient temperature overnight. After this time, the reactionwas cooled to 0° C. and 5.0 ml of water was added. The reaction wasstirred for 10 min. and then partitioned between ethyl acetate an 5%sodium bicarbonate. The organic extracts were dried over magnesiumsulfate and concentrated to 1.09 g of a yellow oil. The crude productwas dissolved in THF, 0.75 g of 4-trifluoromethylphenyl isocyanate wasadded and the mixture was stirred under nitrogen overnight. The reactionwas then concentrated and the crude product chromatographed on silicagel. Trituration with hexane afforded 0.7 g of a beige solid, mp171-173° C. ¹ H NMR (CDCl₃) δ: 2.2 (m, 2H), 3.18 (m, 1H) 4.3-4.5 (m,2H), 7.1-7.4 (m, 8H) (m, 6HO, 9.02 (S, 1H).

EXAMPLE 6 Step A:Methyl-2-(2-bromomethyl)-S-chloro-2,3-dihydro-1-oxo-1H-indene-2-carboxylate

To 50 mL of DMF was added 0.640 g (0.016 mol) 60% sodium hydride. 3.0 g(0.013 mol) methyl S-chloro-2,3-dihydro-1-oxo-1H-indene-2carboxylatedissolved in 10 mL DMF was added dropwise over 10 minutes. The reactionmixture was stirred for 15 minutes and 10.0 g (0.053 mol)1,2-dibromoethane was added all at once. The reaction mixture was heatedat 80° C. for 2h, cooled to room temperature, poured into 200 mL 5% HClsolution and extracted with ether (3×100mL). The ether layer was washedwith water (100mL) and brine (100mL), dried over anhydrous magnesiumsulfate, filtered and concentrated in vacuo to afford a viscous oil. Thecrude product was chromatographed with 25% ethyl acetate/75% hexane aseluent which afforded 2.2 g of a yellow solid. ¹ H NMR (CDCl₃) δ: 2.4(m, 1H), 2.65 (m, 1H), 3.18 (d, 1H), 3.4 (m, 2H), 3.70 (s, 3H), 3.75 (d,1H), 7.3-7.6 (m, 2H), 7.7 (d, 1H).

Step B: Methyl 7-chloro-2,3,4,5-tetrahydro 2[[[4(trifluoromethoxy)phenyl]amino]carbonyl]-4aH-indene[1,2-c]pyridazine-4a-carboxylate.

To a solution of 4.1 g (0.083 mol) hydrazine and 5.0 g (0.083 mol)acetic acid dissolved in 250 mL method was added 5.0 g (0.015 mol) ofthe product obtained from Step A. The reaction mixture was refluxed for18h, concentrated in vacuo and ice and 200 mL saturated sodiumbicarbonate was added. The crude product was extracted with ethylacetate (3×100 mL) washed with water (100 mL) and brine (100 mL), driedover anhydrous magnesium sulfate, filtered and concentrated to afford1.3 g of a yellow solid which was added to 50 mL ethyl acetate. Thissolution was treated with 3.25 g (0.016 mol)4-trifluroomethoxyphenylisocyanate. The reaction mixture was stirred for15 min., concentrated in vacuo, triturated with ether and filtered toafford 0.20 g of an off-white solid, melting point, 192-194° C. ¹ H NMR(CDCl₃) δ: 1.78 (dt, 1H), 2.8 (m, 1H), 3.01 (d, 1H), 3.30 (dt, 1H), 3.55(d, 1H), 3.66 (s, 3H), 4.50 (ddd, 1H), 7.1-7.4 (m, 4H), 7.55 (d, 2H),7.65 (d, 1H), 8.58 (s, 1H), IR (mineral oil) 3366, 1720, 1692 cm⁻¹.

EXAMPLE 7 Step A:1-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-3-pyridazinecarboxylicacid, ethyl ester

To 12.0 g (0.112 mol) of sodium carbonate suspended in 50 mL THF wasadded 5.0 g (0.028 mol) 3-chlorophenyl hydrazine hydrochloride, 6.5 g(0.033 mol) ethyl bromopyruvate and 44.0 g (0.42 mol) styrene. Thereaction mixture was stirred at room temperature for 18 h, filteredthrough a plug of celite, rinsed with methylene chloride andconcentrated under reduced pressure. The crude reaction mixture wasflash chromatographed using 10% EtOAc/90% hexanes as eluent to afford3.2 g of a yellow solid, mp 125-126° C. ¹ H NMR (CDCl₃) δ: 1.39 (t, 3H),1.8-2.3 (m, 3H), 2.7 (d, 1H), 4.35 (m, 2H), 5.12 (bs, 1H), 6.95 (m, 1H),7.0-7.4 (m, 8H).

Step B:1-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-3-pyridazinecarboxylicacid

To 3.2 g (0.0093 mol) of the product from Step A was added 100 mLmethanol and 100 mL 1N sodium hydroxide. The reaction mixture was heatedat reflux for 18 h, cooled to room temperature, poured into 200 mL waterand extracted with ether (1×100 mL). The aqueous phase was acidifiedwith concentrated HCl and extracted with ether (3×100 mL), washed withwater (1×100 mL) and brine (1×100 mL), dried over anhydrous magnesiumsulfate and concentrated under reduced pressure to afford 3.0 g of ayellow solid, mp 157-158° C. ¹ H NMR (CDCl₃) δ: 1.6 (bs, 1H), 1.8-2.4(m, 3H), 2.8 (d, 1H), 5.3 (bs, 1H), 7.0-7.4 (m, 9H).

Step C:1-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-N-[4-(trifluoromethyl)phenyl]-3-pyridazinecarboxamide

To 0.70 g (0.0022 mol) of the product obtained in Step B, dissolved in10 mL toluene, was added 0.625 g (0.0030 mol)α,α,α-trifluoro-p-tolylisocyanate and 0.30 g (0.0029 mol) triethylamine.The reaction mixture was heated at reflux for 18 h, cooled to roomtemperature and concentrated under reduced pressure. The crude productwas triturated with ether to afford 0.50 g of a white solid, mp183°-184° C. ¹ H NMR (CDCl₃) δ: 1.8-2.4 (m, 3H), 2.9 (d, 1H), 5.25 (bs,1H), 6.95-7.4 (m, 9H), 7.7 (ABq, 4H), 9.02 (bs, 1H). IR (mineral oil):3300, 1663 cm⁻¹.

By the general procedures described herein, or obvious modificationsthereof, the compounds of Tables 1 through 12 can be prepared. ##STR36##

                                      TABLE 2                                     __________________________________________________________________________    R.sup.1 R.sup.2     R.sup.3    R.sup.1  R.sup.2     R.sup.3                   __________________________________________________________________________    E is H, Y is H                                                                CF.sub.3                                                                              H           Me         OCF.sub.3                                                                              H           Me                        CF.sub.3                                                                              H           i-Pr       OCF.sub.3                                                                              H           i-Pr                      CF.sub.3                                                                              H           n-Pr       OCF.sub.3                                                                              H           n-Pr                      CF.sub.3                                                                              H           CO.sub.2 Me                                                                              OCF.sub.3                                                                              H           CO.sub.2 Me               CF.sub.3                                                                              H           Ph         OCF.sub.3                                                                              H           Ph                        CF.sub.3                                                                              H           4-FPh      OCF.sub.3                                                                              H           4-FPh                     CF.sub.3                                                                              H           4-ClPh     OCF.sub.3                                                                              H           4-ClPh                    CF.sub.3                                                                              F           Me         OCF.sub.3                                                                              F           Me                        CF.sub.3                                                                              F           i-Pr       OCF.sub.3                                                                              F           i-Pr                      CF.sub.3                                                                              F           n-Pr       OCF.sub.3                                                                              F           n-Pr                      CF.sub.3                                                                              F           CO.sub.2 Me                                                                              OCF.sub.3                                                                              F           CO.sub.2 Me               CF.sub.3                                                                              F           Ph         OCF.sub.3                                                                              F           Ph                        CF.sub.3                                                                              F           4-FPh      OCF.sub.3                                                                              F           4-FPh                     CF.sub.3                                                                              F           4-ClPh     OCF.sub.3                                                                              F           4-ClPh                    CF.sub.3                                                                              Cl          Me         OCF.sub.3                                                                              Cl          Me                        CF.sub.3                                                                              Cl          i-Pr       OCF.sub.3                                                                              Cl          i-Pr                      CF.sub.3                                                                              Cl          n-Pr       OCF.sub.3                                                                              Cl          n-Pr                      CF.sub.3                                                                              Cl          CO.sub.2 Me                                                                              OCF.sub.3                                                                              Cl          CO.sub.2 Me               CF.sub.3                                                                              Cl          Ph         OCF.sub.3                                                                              Cl          Ph                        CF.sub.3                                                                              Cl          4-FPh      OCF.sub.3                                                                              Cl          4-FPh                     CF.sub.3                                                                              Cl          4-ClPh     OCF.sub.3                                                                              Cl          4-ClPh                    CF.sub.3                                                                              CF.sub.3    Me         OCF.sub.3                                                                              CF.sub.3    Me                        CF.sub.3                                                                              CF.sub.3    i-Pr       OCF.sub.3                                                                              CF.sub.3    i-Pr                      CF.sub.3                                                                              CF.sub.3    n-Pr       OCF.sub.3                                                                              CF.sub.3    n-Pr                      CF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                              OCF.sub.3                                                                              CF.sub.3    CO.sub.2 Me               CF.sub.3                                                                              CF.sub.3    Ph         OCF.sub.3                                                                              CF.sub.3    Ph                        CF.sub.3                                                                              CF.sub.3    4-FPh      OCF.sub.3                                                                              CF.sub.3    4-FPh                     CF.sub.3                                                                              CF.sub.3    4-ClPh     OCF.sub.3                                                                              CF.sub.3    4-ClPh                    CF.sub.3                                                                              Br          Me         OCF.sub.3                                                                              Br          Me                        CF.sub.3                                                                              Br          i-Pr       OCF.sub.3                                                                              Br          i-Pr                      CF.sub.3                                                                              Br          n-Pr       OCF.sub.3                                                                              Br          n-Pr                      CF.sub.3                                                                              Br          CO.sub.2 Me                                                                              OCF.sub.3                                                                              Br          CO.sub.2 Me               CF.sub. 3                                                                             Br          Ph         OCF.sub.3                                                                              Br          Ph                        CF.sub.3                                                                              Br          4-FPh      OCF.sub.3                                                                              Br          4-FPh                     CF.sub.3                                                                              Br          4-ClPh     OCF.sub.3                                                                              Br          4-ClPh                    CF.sub.3                                                                              NO.sub.2    Me         OCF.sub.3                                                                              NO.sub.2    Me                        CF.sub.3                                                                              NO.sub.2    i-Pr       OCF.sub.3                                                                              NO.sub.2    i-Pr                      CF.sub.3                                                                              NO.sub.2    n-Pr       OCF.sub.3                                                                              NO.sub.2    n-Pr                      CF.sub.3                                                                              NO.sub.2    CO.sub.2 Me                                                                              OCF.sub.3                                                                              NO.sub.2    CO.sub.2 Me               CF.sub.3                                                                              NO.sub.2    Ph         OCF.sub.3                                                                              NO.sub.2    Ph                        CF.sub.3                                                                              NO.sub.2    4-FPh      OCF.sub.3                                                                              NO.sub.2    4-FPh                     CF.sub.3                                                                              NO.sub.2    4-ClPh     OCF.sub.3                                                                              NO.sub.2    4-ClPh                    CF.sub.3                                                                              CH.sub.3 O  Me         OCF.sub.3                                                                              CH.sub.3 O  Me                        CF.sub.3                                                                              CH.sub.3 O  i-Pr       OCF.sub.3                                                                              CH.sub.3 O  i-Pr                      CF.sub.3                                                                              CH.sub.3 O  n-Pr       OCF.sub.3                                                                              CH.sub.3 O  n-Pr                      CF.sub.3                                                                              CH.sub.3 O  CO.sub.2 Me                                                                              OCF.sub.3                                                                              CH.sub.3 O  CO.sub.2 Me               CF.sub.3                                                                              CH.sub.3 O  Ph         OCF.sub.3                                                                              CH.sub.3 O  Ph                        CF.sub.3                                                                              CH.sub.3 O  4-FPh      OCF.sub.3                                                                              CH.sub.3 O  4-FPh                     CF.sub.3                                                                              CH.sub.3 O  4-ClPh     OCF.sub.3                                                                              CH.sub.3 O  4-ClPh                    CF.sub.3                                                                              CF.sub. 3 CH.sub.2 O                                                                      Me         OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Me                        CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       i-Pr       OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       i-Pr                      CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       n-Pr       OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       n-Pr                      CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me                                                                              OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me               CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Ph         OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Ph                        CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-FPh      OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-FPh                     CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-ClPh     OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-ClPh                    E is H, Y is Me                                                               CF.sub.3                                                                              H           Me         OCF.sub.3                                                                              H           Me                        CF.sub.3                                                                              H           i-Pr       OCF.sub.3                                                                              H           i-Pr                      CF.sub.3                                                                              H           n-Pr       OCF.sub.3                                                                              H           n-Pr                      CF.sub.3                                                                              H           CO.sub.2 Me                                                                              OCF.sub.3                                                                              H           CO.sub.2 Me               CF.sub.3                                                                              H           Ph         OCF.sub.3                                                                              H           Ph                        CF.sub.3                                                                              H           4-FPh      OCF.sub.3                                                                              H           4-FPh                     CF.sub.3                                                                              H           4-ClPh     OCF.sub.3                                                                              H           4-ClPh                    CF.sub.3                                                                              F           Me         OCF.sub. 3                                                                             F           Me                        CF.sub.3                                                                              F           i-Pr       OCF.sub.3                                                                              F           i-Pr                      CF.sub.3                                                                              F           n-Pr       OCF.sub.3                                                                              F           n-Pr                      CF.sub.3                                                                              F           CO.sub.2 Me                                                                              OCF.sub.3                                                                              F           CO.sub.2 Me               CF.sub.3                                                                              F           Ph         OCF.sub.3                                                                              F           Ph                        CF.sub.3                                                                              F           4-FPh      OCF.sub.3                                                                              F           4-FPh                     CF.sub.3                                                                              F           4-ClPh     OCF.sub.3                                                                              F           4-ClPh                    CF.sub.3                                                                              Cl          Me         OCF.sub.3                                                                              Cl          Me                        CF.sub.3                                                                              Cl          i-Pr       OCF.sub.3                                                                              Cl          i-Pr                      CF.sub.3                                                                              Cl          n-Pr       OCF.sub.3                                                                              Cl          n-Pr                      CF.sub.3                                                                              Cl          CO.sub.2 Me                                                                              OCF.sub.3                                                                              Cl          CO.sub.2 Me               CF.sub.3                                                                              Cl          Ph         OCF.sub.3                                                                              Cl          Ph                        CF.sub.3                                                                              Cl          4-FPh      OCF.sub.3                                                                              Cl          4-FPh                     CF.sub.3                                                                              Cl          4-ClPh     OCF.sub.3                                                                              Cl          4-ClPh                    CF.sub.3                                                                              CF.sub.3    Me         OCF.sub.3                                                                              CF.sub.3    Me                        CF.sub.3                                                                              CF.sub.3    i-Pr       OCF.sub.3                                                                              CF.sub.3    i-Pr                      CF.sub.3                                                                              CF.sub.3    n-Pr       OCF.sub.3                                                                              CF.sub.3    n-Pr                      CF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                              OCF.sub.3                                                                              CF.sub.3    CO.sub.2 Me               CF.sub.3                                                                              CF.sub.3    Ph         OCF.sub.3                                                                              CF.sub.3    Ph                        CF.sub.3                                                                              CF.sub.3    4-FPh      OCF.sub.3                                                                              CF.sub.3    4-FPh                     CF.sub.3                                                                              CF.sub.3    4-ClPh     OCF.sub.3                                                                              CF.sub.3    4-ClPh                    E is H, Y is COMe                                                             CF.sub.3                                                                              H           Me         OCF.sub.3                                                                              H           Me                        CF.sub.3                                                                              H           i-Pr       OCF.sub.3                                                                              H           i-Pr                      CF.sub.3                                                                              H           n-Pr       OCF.sub.3                                                                              H           n-Pr                      CF.sub.3                                                                              H           CO.sub.2 Me                                                                              OCF.sub.3                                                                              H           CO.sub.2 Me               CF.sub.3                                                                              H           Ph         OCF.sub.3                                                                              H           Ph                        CF.sub.3                                                                              H           4-FPh      OCF.sub.3                                                                              H           4-FPh                     CF.sub.3                                                                              H           4-ClPh     OCF.sub.3                                                                              H           4-ClPh                    CF.sub.3                                                                              F           Me         OCF.sub.3                                                                              F           Me                        CF.sub.3                                                                              F           i-Pr       OCF.sub.3                                                                              F           i-Pr                      CF.sub.3                                                                              F           n-Pr       OCF.sub.3                                                                              F           n-Pr                      CF.sub.3                                                                              F           CO.sub.2 Me                                                                              OCF.sub.3                                                                              F           CO.sub.2 Me               CF.sub.3                                                                              F           Ph         OCF.sub.3                                                                              F           Ph                        CF.sub.3                                                                              F           4-FPh      OCF.sub.3                                                                              F           4-FPh                     CF.sub.3                                                                              F           4-ClPh     OCF.sub.3                                                                              F           4-ClPh                    CF.sub.3                                                                              Cl          Me         OCF.sub.3                                                                              Cl          Me                        CF.sub.3                                                                              Cl          i-Pr       OCF.sub.3                                                                              Cl          i-Pr                      CF.sub.3                                                                              Cl          n-Pr       OCF.sub.3                                                                              Cl          n-Pr                      CF.sub.3                                                                              Cl          CO.sub.2 Me                                                                              OCF.sub.3                                                                              Cl          CO.sub.2 Me               CF.sub.3                                                                              Cl          Ph         OCF.sub.3                                                                              Cl          Ph                        CF.sub.3                                                                              Cl          4-FPh      OCF.sub.3                                                                              Cl          4-FPh                     CF.sub.3                                                                              Cl          4-Cl Ph    OCF.sub.3                                                                              Cl          4-ClPh                    CF.sub.3                                                                              CF.sub.3    Me         OCF.sub.3                                                                              CF.sub.3    Me                        CF.sub.3                                                                              CF.sub.3    i-Pr       OCF.sub.3                                                                              CF.sub.3    i-Pr                      CF.sub.3                                                                              CF.sub.3    n-Pr       OCF.sub.3                                                                              CF.sub.3    n-Pr                      CF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                              OCF.sub.3                                                                              CF.sub.3    CO.sub.2 Me               CF.sub.3                                                                              CF.sub.3    Ph         OCF.sub.3                                                                              CF.sub.3    Ph                        CF.sub.3                                                                              CF.sub.3    4-FPh      OCF.sub.3                                                                              CF.sub.3    4-FPh                     CF.sub.3                                                                              CF.sub.3    4-ClPh     OCF.sub.3                                                                              CF.sub.3    4-ClPh                    E is H, Y is CO.sub.2 Me                                                      CF.sub.3                                                                              H           Me         OCF.sub.3                                                                              H           Me                        CF.sub.3                                                                              H           i-Pr       OCF.sub.3                                                                              H           i-Pr                      CF.sub.3                                                                              H           n-Pr       OCF.sub.3                                                                              H           n-Pr                      CF.sub.3                                                                              H           CO.sub.2 Me                                                                              OCF.sub.3                                                                              H           CO.sub.2 Me               CF.sub.3                                                                              H           Ph         OCF.sub.3                                                                              H           Ph                        CF.sub.3                                                                              H           4-FPh      OCF.sub.3                                                                              H           4-FPh                     CF.sub.3                                                                              H           4-ClPh     OCF.sub.3                                                                              H           4-ClPh                    CF.sub.3                                                                              F           Me         OCF.sub.3                                                                              F           Me                        CF.sub.3                                                                              F           i-Pr       OCF.sub.3                                                                              F           i-Pr                      CF.sub.3                                                                              F           n-Pr       OCF.sub.3                                                                              F           n-Pr                      CF.sub.3                                                                              F           CO.sub.2 Me                                                                              OCF.sub.3                                                                              F           CO.sub.2 Me               CF.sub. 3                                                                             F           Ph         OCF.sub.3                                                                              F           Ph                        CF.sub.3                                                                              F           4-FPh      OCF.sub.3                                                                              F           4-FPh                     CF.sub.3                                                                              F           4-ClPh     OCF.sub.3                                                                              F           4-ClPh                    CF.sub.3                                                                              Cl          Me         OCF.sub.3                                                                              Cl          Me                        CF.sub.3                                                                              Cl          i-Pr       OCF.sub.3                                                                              Cl          i-Pr                      CF.sub.3                                                                              Cl          n-Pr       OCF.sub.3                                                                              Cl          n-Pr                      CF.sub.3                                                                              Cl          CO.sub.2 Me                                                                              OCF.sub.3                                                                              Cl          CO.sub.2 Me               CF.sub.3                                                                              Cl          Ph         OCF.sub.3                                                                              Cl          Ph                        CF.sub.3                                                                              Cl          4-FPh      OCF.sub.3                                                                              Cl          4-FPh                     CF.sub.3                                                                              Cl          4-ClPh     OCF.sub.3                                                                              Cl          4-ClPh                    CF.sub.3                                                                              CF.sub.3    Me         OCF.sub.3                                                                              CF.sub.3    Me                        CF.sub.3                                                                              CF.sub.3    i-Pr       OCF.sub.3                                                                              CF.sub.3    i-Pr                      CF.sub.3                                                                              CF.sub.3    n-Pr       OCF.sub.3                                                                              CF.sub.3    n-Pr                      CF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                              OCF.sub.3                                                                              CF.sub.3    CO.sub.2 Me               CF.sub.3                                                                              CF.sub.3    Ph         OCF.sub.3                                                                              CF.sub.3    Ph                        CF.sub.3                                                                              CF.sub.3    4-FPh      OCF.sub.3                                                                              CF.sub.3    4-FPh                     CF.sub.3                                                                              CF.sub.3    4-ClPh     OCF.sub.3                                                                              CF.sub.3    4-ClPh                    E is Me, Y is H                                                               CF.sub.3                                                                              H           Me         OCF.sub.3                                                                              H           Me                        CF.sub.3                                                                              H           i-Pr       OCF.sub.3                                                                              H           i-Pr                      CF.sub. 3                                                                             H           n-Pr       OCF.sub.3                                                                              H           n-Pr                      CF.sub.3                                                                              H           CO.sub.2 Me                                                                              OCF.sub.3                                                                              H           CO.sub.2 Me               CF.sub.3                                                                              H           Ph         OCF.sub.3                                                                              H           Ph                        CF.sub.3                                                                              H           4-FPh      OCF.sub.3                                                                              H           4-FPh                     CF.sub.3                                                                              H           4-ClPh     OCF.sub.3                                                                              H           4-ClPh                    CF.sub.3                                                                              F           Me         OCF.sub.3                                                                              F           Me                        CF.sub.3                                                                              F           i-Pr       OCF.sub.3                                                                              F           i-Pr                      CF.sub.3                                                                              F           n-Pr       OCF.sub.3                                                                              F           n-Pr                      CF.sub.3                                                                              F           CO.sub.2 Me                                                                              OCF.sub.3                                                                              F           CO.sub.2 Me               CF.sub.3                                                                              F           Ph         OCF.sub.3                                                                              F           Ph                        CF.sub.3                                                                              F           4-FPh      OCF.sub.3                                                                              F           4-FPh                     CF.sub.3                                                                              F           4-ClPh     OCF.sub.3                                                                              F           4-ClPh                    CF.sub.3                                                                              Cl          Me         OCF.sub.3                                                                              Cl          Me                        CF.sub.3                                                                              Cl          i-Pr       OCF.sub.3                                                                              Cl          i-Pr                      CF.sub.3                                                                              Cl          n-Pr       OCF.sub.3                                                                              Cl          n-Pr                      CF.sub.3                                                                              Cl          CO.sub.2 Me                                                                              OCF.sub.3                                                                              Cl          CO.sub.2 Me               CF.sub.3                                                                              Cl          Ph         OCF.sub.3                                                                              Cl          Ph                        CF.sub.3                                                                              Cl          4-FPh      OCF.sub.3                                                                              Cl          4-FPh                     CF.sub.3                                                                              Cl          4-ClPh     OCF.sub.3                                                                              Cl          4-ClPh                    CF.sub.3                                                                              CF.sub.3    Me         OCF.sub.3                                                                              CF.sub.3    Me                        CF.sub.3                                                                              CF.sub.3    i-Pr       OCF.sub.3                                                                              CF.sub.3    i-Pr                      CF.sub.3                                                                              CF.sub.3    n-Pr       OCF.sub.3                                                                              CF.sub.3    n-Pr                      CF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                              OCF.sub.3                                                                              CF.sub.3    CO.sub.2 Me               CF.sub.3                                                                              CF.sub.3    Ph         OCF.sub.3                                                                              CF.sub.3    Ph                        CF.sub.3                                                                              CF.sub.3    4-FPh      OCF.sub.3                                                                              CF.sub.3    4-FPh                     CF.sub.3                                                                              CF.sub.3    4-ClPh     OCF.sub.3                                                                              CF.sub.3    4-ClPh                    CF.sub.3                                                                              Br          Me         OCF.sub.3                                                                              Br          Me                        CF.sub.3                                                                              Br          i-Pr       OCF.sub.3                                                                              Br          i-Pr                      CF.sub.3                                                                              Br          n-Pr       OCF.sub.3                                                                              Br          n-Pr                      CF.sub.3                                                                              Br          CO.sub.2 Me                                                                              OCF.sub.3                                                                              Br          CO.sub.2 Me               CF.sub.3                                                                              Br          Ph         OCF.sub.3                                                                              Br          Ph                        CF.sub.3                                                                              Br          4-FPh      OCF.sub.3                                                                              Br          4-FPh                     CF.sub.3                                                                              Br          4-ClPh     OCF.sub.3                                                                              Br          4-ClPh                    CF.sub.3                                                                              NO.sub.2    Me         OCF.sub.3                                                                              NO.sub.2    Me                        CF.sub.3                                                                              NO.sub.2    i-Pr       OCF.sub.3                                                                              NO.sub.2    i-Pr                      CF.sub.3                                                                              NO.sub.2    n-Pr       OCF.sub.3                                                                              NO.sub.2    n-Pr                      CF.sub.3                                                                              NO.sub.2    CO.sub.2 Me                                                                              OCF.sub.3                                                                              NO.sub.2    CO.sub.2 Me               CF.sub.3                                                                              NO.sub.2    Ph         OCF.sub.3                                                                              NO.sub.2    Ph                        CF.sub.3                                                                              NO.sub.2    4-FPh      OCF.sub.3                                                                              NO.sub.2    4-FPh                     CF.sub.3                                                                              NO.sub.2    4-ClPh     OCF.sub.3                                                                              NO.sub.2    4-ClPh                    CF.sub.3                                                                              CH.sub.3 O  Me         OCF.sub.3                                                                              CH.sub.3 O  Me                        CF.sub.3                                                                              CH.sub.3 O  i-Pr       OCF.sub.3                                                                              CH.sub.3 O  i-Pr                      CF.sub.3                                                                              CH.sub.3 O  n-Pr       OCF.sub.3                                                                              CH.sub.3 O  n-Pr                      CF.sub.3                                                                              CH.sub.3 O  CO.sub.2 Me                                                                              OCF.sub.3                                                                              CH.sub.3 O  CO.sub.2 Me               CF.sub.3                                                                              CH.sub.3 O  Ph         OCF.sub.3                                                                              CH.sub.3 O  Ph                        CF.sub.3                                                                              CH.sub.3 O  4-FPh      OCF.sub.3                                                                              CH.sub.3 O  4-FPh                     CF.sub.3                                                                              CH.sub.3 O  4-ClPh     OCF.sub.3                                                                              CH.sub.3 O  4-ClPh                    CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Me         OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Me                        CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       i-Pr       OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       i-Pr                      CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       n-Pr       OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       n-Pr                      CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me                                                                              OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me               CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Ph         OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Ph                        CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-FPh      OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-FPh                     CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-ClPh     OCF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-ClPh                    __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR37##                                                                    R.sup.1   R.sup.2   R.sup.3    R.sup.1   R.sup.2   R.sup.3                    __________________________________________________________________________    V is CH.sub.2                                                                 CF.sub.3  6-F       i-Pr       OCF.sub.3 6-F       i-Pr                       CF.sub.3  6-F       n-Pr       OCF.sub.3 6-F       n-Pr                       CF.sub.3  6-F       CO.sub.2 Me                                                                              OCF.sub.3 6-F       CO.sub.2 Me                CF.sub.3  6-F       4-FPh      OCF.sub.3 6-F       4-FPh                      CF.sub.3  6-Cl      i-Pr       OCF.sub.3 6-Cl      i-Pr                       CF.sub.3  6-Cl      n-Pr       OCF.sub.3 6-Cl      n-Pr                       CF.sub.3  6-Cl      CO.sub.2 Me                                                                              OCF.sub.3 6-Cl      CO.sub.2 Me                CF.sub.3  6-Cl      4-FPh      OCF.sub.3 6-Cl      4-FPh                      CF.sub.3  7-F       i-Pr       OCF.sub.3 7-F       i-Pr                       CF.sub.3  7-F       n-Pr       OCF.sub.3 7-F       n-Pr                       CF.sub.3  7-F       CO.sub.2 Me                                                                              OCF.sub.3 7-F       CO.sub.2 Me                CF.sub.3  7-F       4-FPh      OCF.sub.3 7-F       4-FPh                      CF.sub.3  7-Cl      i-Pr       OCF.sub.3 7-Cl      i-Pr                       CF.sub.3  7-Cl      n-Pr       OCF.sub.3 7-Cl      n-Pr                       CF.sub.3  7-Cl      CO.sub.2 Me                                                                              OCF.sub.3 7-Cl      CO.sub.2 Me                CF.sub.3  7-Cl      4-FPh      OCF.sub.3 7-Cl      4-FPh                      CF.sub.3  7-CF.sub.3                                                                              i-Pr       OCF.sub.3 7-CF.sub.3                                                                              i-Pr                       CF.sub.3  7-CF.sub.3                                                                              n-Pr       OCF.sub.3 7-CF.sub.3                                                                              n-Pr                       CF.sub.3  7-CF.sub.3                                                                              CO.sub.2 Me                                                                              OCF.sub.3 7-CF.sub.3                                                                              CO.sub.2 Me                CF.sub.3  7-CF.sub.3                                                                              4-FPh      OCF.sub.3 7-CF.sub.3                                                                              4-FPh                      V is OCH.sub.2                                                                CF.sub.3  6-F       i-Pr                                                      CF.sub.3  6-F       CO.sub.2 Me                                               CF.sub.3  6-F       4-FPh                                                     OCF.sub.3 6-F       i-Pr                                                      OCF.sub.3 6-F       CO.sub.2 Me                                               OCF.sub.3 6-F       4-FPh                                                     CF.sub.3  6-Cl      i-Pr                                                      CF.sub.3  6-Cl      CO.sub.2 Me                                               CF.sub.3  6-Cl      4-FPh                                                     OCF.sub.3 6-Cl      i-Pr                                                      OCF.sub.3 6-Cl      CO.sub.2 Me                                               OCF.sub.3 6-Cl      4-FPh                                                     __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________     ##STR38##                                                                    R.sup.1  R.sup.2 R.sup.3       R.sup.1  R.sup.2  R.sup.3                      __________________________________________________________________________    Y is H                                                                        CF.sub.3 H       Ph            OCF.sub.3                                                                              H        Ph                           CF.sub.3 H       4-FPh         OCF.sub.3                                                                              H        4-FPh                        CF.sub.3 H       4-ClPh        OCF.sub.3                                                                              H        4-ClPh                       CF.sub.3 H       4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              H        4-CO.sub.2 MePh              CF.sub.3 F       Ph            OCF.sub.3                                                                              F        Ph                           CF.sub.3 F       4-FPh         OCF.sub.3                                                                              F        4-FPh                        CF.sub.3 F       4-ClPh        OCF.sub.3                                                                              F        4-ClPh                       CF.sub.3 F       4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              F        4-CO.sub.2 MePh              CF.sub.3 Cl      Ph            OCF.sub.3                                                                              Cl       Ph                           CF.sub.3 Cl      4-FPh         OCF.sub.3                                                                              Cl       4-FPh                        CF.sub.3 Cl      4-ClPh        OCF.sub.3                                                                              Cl       4-ClPh                       CF.sub.3 Cl      4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              Cl       4-CO.sub.2 MePh              CF.sub.3 Br      Ph            OCF.sub.3                                                                              Br       Ph                           CF.sub.3 Br      4-FPh         OCF.sub.3                                                                              Br       4-FPh                        CF.sub.3 Br      4-ClPh        OCF.sub.3                                                                              Br       4-ClPh                       CF.sub.3 Br      4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              Br       4-CO.sub.2 MePh              CF.sub.3 CF.sub.3                                                                              Ph            OCF.sub.3                                                                              CF.sub.3 Ph                           CF.sub.3 CF.sub.3                                                                              4-FPh         OCF.sub.3                                                                              CF.sub.3 4-FPh                        CF.sub.3 CF.sub.3                                                                              4-ClPh        OCF.sub.3                                                                              CF.sub.3 4-ClPh                       CF.sub.3 CF.sub.3                                                                              4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              CF.sub.3 4-CO.sub.2 MePh              Y is CO.sub.2 Me                                                              CF.sub.3 H       Ph            OCF.sub.3                                                                              H        Ph                           CF.sub.3 H       4-FPh         OCF.sub.3                                                                              H        4-FPh                        CF.sub.3 H       4-ClPh        OCF.sub.3                                                                              H        4-ClPh                       CF.sub.3 H       4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              H        4-CO.sub.2 MePh              CF.sub.3 F       Ph            OCF.sub.3                                                                              F        Ph                           CF.sub.3 F       4-FPh         OCF.sub.3                                                                              F        4-FPh                        CF.sub.3 F       4-ClPh        OCF.sub.3                                                                              F        4-ClPh                       CF.sub.3 F       4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              F        4-CO.sub.2 MePh              CF.sub.3 Cl      Ph            OCF.sub.3                                                                              Cl       Ph                           CF.sub.3 Cl      4-FPh         OCF.sub.3                                                                              Cl       4-FPh                        CF.sub.3 Cl      4-ClPh        OCF.sub.3                                                                              Cl       4-ClPh                       CF.sub.3 Cl      4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              Cl       4-CO.sub.2 MePh              CF.sub.3 Br      Ph            OCF.sub.3                                                                              Br       Ph                           CF.sub.3 Br      4-FPh         OCF.sub.3                                                                              Br       4-FPh                        CF.sub.3 Br      4-ClPh        OCF.sub.3                                                                              Br       4-ClPh                       CF.sub.3 Br      4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              Br       4-CO.sub.2 MePh              CF.sub.3 CF.sub.3                                                                              Ph            OCF.sub.3                                                                              CF.sub.3 Ph                           CF.sub.3 CF.sub.3                                                                              4-FPh         OCF.sub.3                                                                              CF.sub.3 4-FPh                        CF.sub.3 CF.sub.3                                                                              4-ClPh        OCF.sub.3                                                                              CF.sub.3 4-ClPh                       CF.sub.3 CF.sub.3                                                                              4-CO.sub.2 MePh                                                                             OCF.sub.3                                                                              CF.sub.3 4-CO.sub.2 MePh              __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________     ##STR39##                                                                    R.sup.1 R.sup.2     R.sup.3    R.sup.1   R.sup.2     R.sup.3                  __________________________________________________________________________    E is H, Y is H                                                                CF.sub.3                                                                              H           Me         OCF.sub.3 H           Me                       CF.sub.3                                                                              H           i-Pr       OCF.sub.3 H           i-Pr                     CF.sub.3                                                                              H           n-Pr       OCF.sub.3 H           n-Pr                     CF.sub.3                                                                              H           CO.sub.2 Me                                                                              OCF.sub.3 H           CO.sub.2 Me              CF.sub.3                                                                              H           Ph         OCF.sub.3 H           Ph                       CF.sub.3                                                                              H           4-FPh      OCF.sub.3 H           4-FPh                    CF.sub.3                                                                              H           4-ClPh     OCF.sub.3 H           4-ClPh                   CF.sub.3                                                                              F           Me         OCF.sub.3 F           Me                       CF.sub.3                                                                              F           i-Pr       OCF.sub.3 F           i-Pr                     CF.sub.3                                                                              F           n-Pr       OCF.sub.3 F           n-Pr                     CF.sub.3                                                                              F           CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3                                                                              F           Ph         OCF.sub.3 F           Ph                       CF.sub.3                                                                              F           4-FPh      OCF.sub.3 F           4-F-ph                   CF.sub.3                                                                              F           4-ClPh     OCF.sub.3 F           4-ClPh                   CF.sub.3                                                                              Cl          Me         OCF.sub.3 Cl          Me                       CF.sub.3                                                                              Cl          i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3                                                                              Cl          n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3                                                                              Cl          CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3                                                                              Cl          Ph         OCF.sub.3 Cl          Ph                       CF.sub.3                                                                              Cl          4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3                                                                              Cl          4-ClPh     OCF.sub.3 Cl          4-ClPh                   CF.sub.3                                                                              CF.sub.3    Me         OCF.sub.3 CF.sub.3    Me                       CF.sub.3                                                                              CF.sub.3    i-Pr       OCF.sub.3 CF.sub.3    i-Pr                     CF.sub.3                                                                              CF.sub.3    n-Pr       OCF.sub.3 CF.sub.3    n-Pr                     CF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub.2 Me              CF.sub.3                                                                              CF.sub.3    Ph         OCF.sub.3 CF.sub.3    Ph                       CF.sub.3                                                                              CF.sub.3    4-FPh      OCF.sub.3 CF.sub.3    4-FPh                    CF.sub.3                                                                              CF.sub.3    4-ClPh     OCF.sub.3 CF.sub.3    4-ClPh                   CF.sub.3                                                                              Br          Me         OCF.sub.3 Br          Me                       CF.sub.3                                                                              Br          i-Pr       OCF.sub.3 Br          i-Pr                     CF.sub.3                                                                              Br          n-Pr       OCF.sub.3 Br          n-Pr                     CF.sub.3                                                                              Br          CO.sub.2 Me                                                                              OCF.sub. 3                                                                              Br          CO.sub.2 Me              CF.sub.3                                                                              Br          Ph         OCF.sub.3 Br          Ph                       CF.sub.3                                                                              Br          4-FPh      OCF.sub.3 Br          4-FPh                    CF.sub.3                                                                              Br          4-ClPh     OCF.sub.3 Br          4-ClPh                   CF.sub.3                                                                              NO.sub.2    Me         OCF.sub.3 NO.sub.2    Me                       CF.sub.3                                                                              NO.sub.2    i-Pr       OCF.sub.3 NO.sub.2    i-Pr                     CF.sub.3                                                                              NO.sub.2    n-Pr       OCF.sub.3 NO.sub.2    n-Pr                     CF.sub.3                                                                              NO.sub.2    CO.sub.2 Me                                                                              OCF.sub.3 NO.sub.2    CO.sub.2 Me              CF.sub.3                                                                              NO.sub.2    Ph         OCF.sub.3 NO.sub.2    Ph                       CF.sub.3                                                                              NO.sub.2    4-FPh      OCF.sub.3 NO.sub.2    4-FPh                    CF.sub.3                                                                              NO.sub.2    4-ClPh     OCF.sub.3 NO.sub.2    4-ClPh                   CF.sub.3                                                                              CH.sub.3 O  Me         OCF.sub.3 CH.sub.3 O  Me                       CF.sub.3                                                                              CH.sub.3 O  i-Pr       OCF.sub.3 CH.sub.3 O  i-Pr                     CF.sub.3                                                                              CH.sub.3 O  n-Pr       OCF.sub.3 CH.sub.3 O  n-Pr                     CF.sub.3                                                                              CH.sub.3 O  CO.sub.2 Me                                                                              OCF.sub.3 CH.sub.3 O  CO.sub.2 Me              CF.sub.3                                                                              CH.sub.3 O  Ph         OCF.sub.3 CH.sub.3 O  Ph                       CF.sub.3                                                                              CH.sub.3 O  4-FPh      OCF.sub.3 CH.sub.3 O  4-FPh                    CF.sub.3                                                                              CH.sub.3 O  4-ClPh     OCF.sub.3 CH.sub.3 O  4-ClPh                   CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Me         OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       Me                       CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       i-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       i-Pr                     CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       n-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       n-Pr                     CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me              CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Ph         OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       Ph                       CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-FPh      OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       4-FPh                    CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-ClPh     OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       4-ClPh                   E is Me, Y is H                                                               CF.sub.3                                                                              H           Me         OCF.sub.3 H           Me                       CF.sub.3                                                                              H           i-Pr       OCF.sub.3 H           i-Pr                     CF.sub.3                                                                              H           n-Pr       OCF.sub.3 H           n-Pr                     CF.sub.3                                                                              H           CO.sub.2 Me                                                                              OCF.sub.3 H           CO.sub.2 Me              CF.sub.3                                                                              H           Ph         OCF.sub.3 H           Ph                       CF.sub.3                                                                              H           4-FPh      OCF.sub.3 H           4-FPh                    CF.sub.3                                                                              H           4-ClPh     OCF.sub.3 H           4-ClPh                   CF.sub.3                                                                              F           Me         OCF.sub.3 F           Me                       CF.sub.3                                                                              F           i-Pr       OCF.sub.3 F           i-Pr                     CF.sub.3                                                                              F           n-Pr       OCF.sub.3 F           n-Pr                     CF.sub.3                                                                              F           CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3                                                                              F           Ph         OCF.sub.3 F           Ph                       CF.sub.3                                                                              F           4-FPh      OCF.sub.3 F           4-FPh                    CF.sub.3                                                                              F           4-ClPh     OCF.sub.3 F           4-ClPh                   CF.sub.3                                                                              Cl          Me         OCF.sub.3 Cl          Me                       CF.sub.3                                                                              Cl          i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3                                                                              Cl          n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3                                                                              Cl          CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3                                                                              Cl          Ph         OCF.sub.3 Cl          Ph                       CF.sub.3                                                                              Cl          4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3                                                                              Cl          4-ClPh     OCF.sub.3 Cl          4-ClPh                   CF.sub.3                                                                              CF.sub.3    Me         OCF.sub.3 CF.sub.3    Me                       CF.sub.3                                                                              CF.sub.3    i-Pr       OCF.sub.3 CF.sub.3    i-Pr                     CF.sub.3                                                                              CF.sub.3    n-Pr       OCF.sub.3 CF.sub.3    n-Pr                     CF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub.2 Me              CF.sub.3                                                                              CF.sub.3    Ph         OCF.sub.3 CF.sub.3    Ph                       CF.sub.3                                                                              CF.sub.3    4-FPh      OCF.sub.3 CF.sub.3    4-FPh                    CF.sub.3                                                                              CF.sub.3    4-ClPh     OCF.sub.3 CF.sub.3    4-ClPh                   CF.sub.3                                                                              Br          Me         OCF.sub.3 Br          Me                       CF.sub.3                                                                              Br          i-Pr       OCF.sub.3 Br          i-Pr                     CF.sub.3                                                                              Br          n-Pr       OCF.sub.3 Br          n-Pr                     CF.sub.3                                                                              Br          CO.sub.2 Me                                                                              OCF.sub.3 Br          CO.sub.2 Me              CF.sub.3                                                                              Br          Ph         OCF.sub.3 Br          Ph                       CF.sub.3                                                                              Br          4-FPh      OCF.sub.3 Br          4-FPh                    CF.sub.3                                                                              Br          4-ClPh     OCF.sub.3 Br          4-ClPh                   CF.sub.3                                                                              NO.sub.2    Me         OCF.sub.3 NO.sub.2    Me                       CF.sub.3                                                                              NO.sub.2    i-Pr       OCF.sub.3 NO.sub.2    i-Pr                     CF.sub.3                                                                              NO.sub.2    n-Pr       OCF.sub.3 NO.sub.2    n-Pr                     CF.sub.3                                                                              NO.sub.2    CO.sub.2 Me                                                                              OCF.sub.3 NO.sub.2    CO.sub.2 Me              CF.sub.3                                                                              NO.sub.2    Ph         OCF.sub.3 NO.sub.2    Ph                       CF.sub.3                                                                              NO.sub.2    4-FPh      OCF.sub.3 NO.sub.2    4-FPh                    CF.sub.3                                                                              NO.sub.2    4-ClPh     OCF.sub.3 NO.sub.2    4-ClPh                   CF.sub.3                                                                              CH.sub.3 O  Me         OCF.sub.3 CH.sub.3 O  Me                       CF.sub.3                                                                              CH.sub.3 O  i-Pr       OCF.sub.3 CH.sub.3 O  i-Pr                     CF.sub.3                                                                              CH.sub.3 O  n-Pr       OCF.sub.3 CH.sub.3 O  n-Pr                     CF.sub.3                                                                              CH.sub.3 O  CO.sub.2 Me                                                                              OCF.sub.3 CH.sub.3 O  CO.sub.2 Me              CF.sub.3                                                                              CH.sub.3 O  Ph         OCF.sub.3 CH.sub.3 O  Ph                       CF.sub.3                                                                              CH.sub.3 O  4-FPh      OCF.sub.3 CH.sub.3 O  4-FPh                    CF.sub.3                                                                              CH.sub.3 O  4-ClPh     OCF.sub.3 CH.sub.3 O  4-ClPh                   CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Me         OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       Me                       CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       i-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       i-Pr                     CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       n-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       n-Pr                     CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me              CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       Ph         OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       Ph                       CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-FPh      OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       4-FPh                    CF.sub.3                                                                              CF.sub.3 CH.sub.2 O                                                                       4-ClPh     OCF       CF CH2O     4-ClPh                   __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________     ##STR40##                                                                    R.sup.1 R.sup.2      R.sup.3   R.sup.1   R.sup.2     R.sup.3                  __________________________________________________________________________    V is CH.sub.2, X is Cl                                                        CF.sub.3                                                                              6-F          i-Pr      OCF.sub.3 6-F         i-Pr                     CF.sub.3                                                                              6-F          n-Pr      OCF.sub.3 6-F         n-Pr                     CF.sub.3                                                                              6-F          CO.sub.2 Me                                                                             OCF       6-F         Me                       CF.sub.3                                                                              6-F          4-FPh     OCF.sub.3 6-F         4-FPh                    CF.sub.3                                                                              6-Cl         i-Pr      OCF.sub.3 6-Cl        i-Pr                     CF.sub.3                                                                              6-Cl         n-Pr      OCF       6-Cl        n-Pr                     CF.sub.3                                                                              6-Cl         CO.sub.2 Me                                                                             OCF.sub.3 6-Cl        CO.sub.2 Me              CF.sub.3                                                                              6-Cl         4-FPh     OCF.sub.3 6-Cl        4-FPh                    CF.sub.3                                                                              7-F          i-Pr      OCF.sub.3 7-F         i-Pr                     CF.sub.3                                                                              7-F          n-Pr      OCF.sub.3 7-F         n-Pr                     CF.sub.3                                                                              7-F          CO.sub.2 Me                                                                             OCF.sub.3 7-F         CO.sub.2 Me              CF.sub. 3                                                                             7-F          4-FPh     OCF.sub.3 7-F         4-FPh                    CF.sub.3                                                                              7-Cl         i-Pr      OCF.sub.3 7-Cl        i-Pr                     CF.sub.3                                                                              7-Cl         n-Pr      OCF.sub.3 7-Cl        n-Pr                     CF.sub.3                                                                              7-Cl         CO.sub.2 Me                                                                             OCF.sub.3 7-Cl        CO.sub.2 Me              CF.sub.3                                                                              7-Cl         4-FPh     OCF.sub.3 7-Cl        4-FPh                    CF.sub.3                                                                              7-CF.sub.3   i-Pr      OCF.sub.3 7-CF.sub.3  i-Pr                     CF.sub.3                                                                              7-CF.sub.3   n-Pr      OCF.sub.3 7-CF.sub.3  n-Pr                     CF.sub.3                                                                              7-CF.sub.3   CO.sub.2 Me                                                                             OCF.sub.3 7-CF.sub.3  CO.sub.2 Me              CF.sub.3                                                                              7-CF.sub.3   4-FPh     OCF.sub.3 7-CF.sub.3  4-FPh                    CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       i-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      i-Pr                     CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       n-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      n-Pr                     CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       CO.sub.2 Me                                                                             OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      CO.sub.2 Me              CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       4-FPh     OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      4-FPh                    V is CH.sub.2, X is OMe                                                       CF.sub.3                                                                              6-F          i-Pr      OCF.sub.3 6-F         i-Pr                     CF.sub.3                                                                              6-F          n-Pr      OCF.sub.3 6-F         n-Pr                     CF.sub.3                                                                              6-F          CO.sub.2 Me                                                                             OCF.sub.3 6-F         CO.sub.2 Me              CF.sub. 3                                                                             6-F          4-FPh     OCF.sub.3 6-F         4-FPh                    CF.sub.3                                                                              6-Cl         i-Pr      OCF.sub.3 6-Cl        i-Pr                     CF.sub.3                                                                              6-Cl         n-Pr      OCF.sub.3 6-Cl        n-Pr                     CF.sub.3                                                                              6-Cl         CO.sub.2 Me                                                                             OCF.sub.3 6-Cl        CO.sub.2 Me              CF.sub.3                                                                              6-Cl         4-FPh     OCF.sub.3 6-Cl        4-FPh                    CF.sub.3                                                                              7-F          i-Pr      OCF.sub.3 7-F         i-Pr                     CF.sub.3                                                                              7-F          n-Pr      OCF.sub.3 7-F         n-Pr                     CF.sub.3                                                                              7-F          CO.sub.2 Me                                                                             OCF.sub.3 7-F         CO.sub.2 Me              CF.sub.3                                                                              7-F          4-FPh     OCF.sub.3 7-F         4-FPh                    CF.sub.3                                                                              7-Cl         i-Pr      OCF.sub.3 7-Cl        i-Pr                     CF.sub.3                                                                              7-Cl         n-Pr      OCF.sub.3 7-Cl        n-Pr                     CF.sub.3                                                                              7-Cl         CO.sub.2 Me                                                                             OCF.sub.3 7-Cl        CO.sub.2 Me              CF.sub.3                                                                              7-Cl         4-FPh     OCF.sub.3 7-Cl        4-FPh                    CF.sub.3                                                                              7-CF.sub.3   i-Pr      OCF.sub.3 7-CF.sub.3  4-FPh                    CF.sub.3                                                                              7-CF.sub.3   n-Pr      OCF.sub.3 7-CF.sub.3  i-Pr                     CF.sub.3                                                                              7-CF.sub.3   CO.sub.2 Me                                                                             OCF.sub.3 7-CF.sub.3  CO.sub.2 Me              CF.sub.3                                                                              7-CF.sub.3   4-FPh     OCF.sub.3 7-CF.sub.3  4-FPh                    CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       i-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      i-Pr                     CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       n-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      n-Pr                     CF.sub.3                                                                              7-OCH2CF     CO.sub.2 Me                                                                             OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      CO.sub.2 Me              CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       4-FPh     OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      4-FPh                    V is O, X is Cl                                                               CF.sub.3                                                                              6-F          i-Pr      OCF.sub.3 6-F         i-Pr                     CF.sub.3                                                                              6-F          n-Pr      OCF.sub.3 6-F         n-Pr                     CF.sub.3                                                                              6-F          CO.sub.2 Me                                                                             OCF.sub.3 6-F         CO.sub.2 Me              CF.sub.3                                                                              6-F          4-FPh     OCF.sub.3 6-F         4-FPh                    CF.sub.3                                                                              6-Cl         i-Pr      OCF.sub.3 6-Cl        i-Pr                     CF.sub.3                                                                              6-Cl         n-Pr      OCF.sub.3 6-Cl        n-Pr                     CF.sub.3                                                                              6-Cl         CO.sub.2 Me                                                                             OCF.sub.3 6-Cl        CO.sub.2 Me              CF.sub.3                                                                              6-Cl         4-FPh     OCF.sub.3 6-Cl        4-FPh                    CF.sub.3                                                                              7-F          i-Pr      OCF.sub.3 7-F         i-Pr                     CF.sub.3                                                                              7-F          n-Pr      OCF.sub.3 7-F         n-Pr                     CF.sub.3                                                                              7-F          CO.sub.2 Me                                                                             OCF.sub.3 7-F         CO.sub.2 Me              CF.sub.3                                                                              7-F          4-FPh     OCF.sub.3 7-F         4-FPh                    CF.sub.3                                                                              7-Cl         i-Pr      OCF.sub.3 7-Cl        i-Pr                     CF.sub.3                                                                              7-Cl         n-Pr      OCF.sub.3 7-Cl        n-Pr                     CF.sub.3                                                                              7-Cl         CO.sub.2 Me                                                                             OCF.sub.3 7-Cl        CO.sub.2 Me              CF.sub.3                                                                              7-Cl         4-FPh     OCF.sub.3 7-Cl        4-FPh                    CF.sub.3                                                                              7-CF.sub.3   i-Pr      OCF.sub. 3                                                                              7-CF.sub.3  i-Pr                     CF.sub.3                                                                              7-CF.sub.3   n-Pr      OCF.sub.3 7-CF.sub.3  n-Pr                     CF.sub.3                                                                              7-CF.sub.3   CO.sub.2 Me                                                                             OCF.sub.3 7-CF.sub.3  CO.sub.2 Me              CF.sub.3                                                                              7-CF.sub.3   4-FPh     OCF.sub.3 7-CF.sub.3  4-FPh                    CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       i-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      i-Pr                     CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       n-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      n-Pr                     CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       CO.sub.2 Me                                                                             OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      CO.sub.2 Me              CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       4-FPh     OCF       7-OCH.sub.2 CF.sub.3                                                                      4-FPh                    V is O, X is OMe                                                              CF.sub.3                                                                              6-F          i-Pr      OCF.sub.3 6-F         i-Pr                     CF.sub.3                                                                              6-F          n-Pr      OCF.sub.3 6-F         n-Pr                     CF.sub.3                                                                              6-F          CO.sub.2 Me                                                                             OCF.sub.3 6-F         CO.sub.2 Me              CF.sub.3                                                                              6-F          4-FPh     OCF.sub.3 6-F         4-FPh                    CF.sub.3                                                                              6-Cl         i-Pr      OCF.sub.3 6-Cl        i-Pr                     CF.sub.3                                                                              6-Cl         n-Pr      OCF.sub.3 6-Cl        n-Pr                     CF.sub.3                                                                              6-Cl         CO.sub.2 Me                                                                             OCF.sub.3 6-Cl        CO.sub.2 Me              CF.sub.3                                                                              6-Cl         4-FPh     OCF.sub.3 6-Cl        4-FPh                    CF.sub.3                                                                              7-F          i-Pr      OCF.sub.3 7-F         i-Pr                     CF.sub. 3                                                                             7-F          n-Pr      OCF.sub.3 7-F         n-Pr                     CF.sub.3                                                                              7-F          CO.sub.2 Me                                                                             OCF.sub.3 7-F         CO.sub.2 Me              CF.sub.3                                                                              7-F          4-FPh     OCF.sub.3 7-F         4-FPh                    CF.sub.3                                                                              7-Cl         i-Pr      OCF.sub.3 7-Cl        i-Pr                     CF.sub.3                                                                              7-Cl         n-Pr      OCF.sub.3 7-Cl        n-Pr                     CF.sub.3                                                                              7-Cl         CO.sub.2 Me                                                                             OCF.sub.3 7-Cl        CO.sub.2 Me              CF.sub.3                                                                              7-Cl         4-FPh     OCF.sub.3 7-Cl        4-FPh                    CF.sub.3                                                                              7-CF.sub.3   i-Pr      OCF.sub.3 7-CF.sub.3  i-Pr                     CF.sub.3                                                                              7-CF.sub.3   n-Pr      OCF.sub.3 7-CF.sub.3  n-Pr                     CF.sub.3                                                                              7-CF.sub.3   CO.sub.2 Me                                                                             OCF.sub.3 7-CF.sub.3  CO.sub.2 Me              CF.sub.3                                                                              7-CF.sub.3   4-FPh     OCF.sub.3 7-CF.sub.3  4-FPh                    CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       i-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      i-Pr                     CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       n-Pr      OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      n-Pr                     CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       CO.sub.2 Me                                                                             OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      CO.sub.2 Me              CF.sub.3                                                                              7-OCH.sub.2 CF.sub.3                                                                       4-FPh     OCF.sub.3 7-OCH.sub.2 CF.sub.3                                                                      4-FPh                    __________________________________________________________________________

                                      TABLE 7                                     __________________________________________________________________________     ##STR41##                                                                    R.sup.1  R.sup.2    R.sup.3    R.sup.1   R.sup.2     R.sup.3                  __________________________________________________________________________    E is H, X is Cl                                                               CF.sub.3 F          i-Pr       OCF.sub.3 F           i-Pr                     CF.sub.3 F          n-Pr       OCF.sub.3 F           n-Pr                     CF.sub.3 F          CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3 F          4-FPh      OCF.sub.3 F           4-FPh                    CF.sub.3 Cl         i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3 Cl         n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3 Cl         CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3 Cl         4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3 Br         i-Pr       OCF.sub.3 Br          i-Pr                     CF.sub.3 Br         n-Pr       OCF.sub.3 Br          n-Pr                     CF.sub.3 Br         CO.sub.2 Me                                                                              OCF.sub.3 Br          CO.sub.2 Me              CF.sub.3 Br         4-FPh      OCF.sub. 3                                                                              Br          4-FPh                    CF.sub.3 CF.sub.3   i-Pr       OCF.sub.3 CF.sub.3    i-Pr                     CF.sub.3 CF.sub.3   n-P r      OCF.sub.3 CF.sub.3    n-Pr                     CF.sub.3 CF.sub.3   CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub.2 Me              CF.sub.3 CF.sub.3   4-FPh      OCF.sub.3 CF.sub.3    4-FPh                    CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      i-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       i-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      n-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       n-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me              CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      4-FPh      OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       4-FPh                    CF.sub.3 MeO        i-Pr       OCF.sub.3 MeO         i-Pr                     CF.sub.3 MeO        n-Pr       OCF.sub.3 MeO         n-Pr                     CF.sub.3 MeO        CO.sub.2 Me                                                                              OCF.sub.3 MeO         CO.sub.2 Me              CF.sub.3 MeO        4-FPh      OCF.sub.3 MeO         4-FPh                    E is H, X is OMe                                                              CF.sub.3 F          i-Pr       OCF.sub.3 F           i-Pr                     CF.sub.3 p          n-Pr       OCF.sub.3 F           n-Pr                     CF.sub.3 F          CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3 F          4-FPh      OCF.sub.3 F           4-FPh                    CF.sub.3 Cl         i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3 Cl         n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3 Cl         CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3 Cl         4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3 Br         i-Pr       OCF.sub.3 Br          i-Pr                     CF.sub.3 Br         n-Pr       OCF.sub.3 Br          n-Pr                     CF.sub.3 Br         CO.sub.2 Me                                                                              OCF.sub.3 Br          CO.sub.2 Me              CF.sub.3 Br         4-FPh      OCF.sub.3 Br          4-FPh                    CF.sub.3 CF.sub.3   i-Pr       OCF.sub.3 CF.sub.3    i-Pr                     CF.sub.3 CF.sub.3   n-Pr       OCF.sub.3 CF.sub.3    n-Pr                     CF.sub.3 CF.sub.3   CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub.2 Me              CF.sub.3 CF.sub.3   4-FPh      OCF.sub.3 CF.sub.3    4-FPh                    CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      i-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       i-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      n-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       n-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me              CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      4-FPh      OCF.sub.3 CF.sub.3 CH.sub.2                                                                         4-F-ph                   CF.sub.3 MeO        i-Pr       OCF.sub.3 MeO         i-Pr                     CF.sub.3 MeO        n-Pr       OCF.sub.3 MeO         n-Pr                     CF.sub.3 MeO        CO.sub.2 Me                                                                              OCF.sub.3 MeO         CO.sub.2 Me              CF.sub.3 MeO        4-FPh      OCF.sub.3 MeO         4-FPh                    E is Me, X is Cl                                                              CF.sub.3 F          i-Pr       OCF.sub.3 F           i-Pr                     CF.sub.3 F          n-Pr       OCF.sub.3 F           n-Pr                     CF.sub.3 F          CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3 F          4-FPh      OCF.sub.3 F           4-FPh                    CF.sub.3 Cl         i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3 Cl         n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3 Cl         CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3 Cl         4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3 Br         i-Pr       OCF.sub.3 Br          i-Pr                     CF.sub.3 Br         n-Pr       OCF.sub.3 Br          n-Pr                     CF.sub.3 Br         CO.sub.2 Me                                                                              OCF.sub.3 Br          CO.sub.2 Me              CF.sub.3 Br         4-FPh      OCF.sub.3 Br          4-FPh                    CF.sub.3 CF.sub.3   i-Pr       OCF.sub.3 CF.sub.3    i-Pr                     CF.sub.3 CF.sub.3   n-P-r      OCF.sub.3 CF.sub.3    n-Pr                     CF.sub.3 CF.sub.3   CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub. 2 Me             CF.sub.3 CF.sub.3   4-FPh      OCF.sub.3 CF.sub.3    4-FPh                    CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      i-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       i-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      n-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       n-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me              CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      4-FPh      OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       4-FPh                    CF.sub.3 MeO        i-Pr       OCF.sub.3 MeO         i-Pr                     CF.sub.3 MeO        n-Pr       OCF.sub.3 MeO         n-Pr                     CF.sub.3 MeO        CO.sub.2 Me                                                                              OCF.sub.3 MeO         CO.sub.2 Me              CF.sub.3 MeO        4-FPh      OCF.sub.3 MeO         4-F-ph                   E is Me, X is OMe                                                             CF.sub.3 F          i-Pr       OCF.sub.3 F           i-Pr                     CF.sub.3 p          n-Pr       OCF.sub.3 F           n-Pr                     CF.sub.3 F          CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3 F          4-FPh      OCF.sub.3 F           4-F-ph                   CF.sub.3 Cl         i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3 Cl         n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3 Cl         CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3 Cl         4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3 Br         i-Pr       OCF.sub.3 Br          i-Pr                     CF.sub.3 Br         n-Pr       OCF.sub.3 Br          n-Pr                     CF.sub.3 Br         CO.sub.2 Me                                                                              OCF.sub.3 Br          CO.sub.2 Me              CF.sub.3 Br         4-F-ph     OCF.sub.3 Br          4-FPh                    CF.sub.3 CF.sub.3   i-Pr       OCF.sub.3 CF.sub.3    i-Pr                     CF.sub.3 CF.sub.3   n-Pr       OCF.sub.3 CF.sub.3    n-Pr                     CF.sub.3 CF.sub.3   CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub.2 Me              CF.sub.3 CF.sub.3   4-F-ph     OCF.sub.3 CF.sub.3    4-FPh                    CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      i-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       i-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      n-Pr       OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       n-Pr                     CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       CO.sub.2 Me              CF.sub.3 CF.sub.3 CH.sub.2 O                                                                      4-FPh      OCF.sub.3 CF.sub.3 CH.sub.2 O                                                                       4-FPh                    CF.sub.3 MeO        i-Pr       OCF.sub.3 MeO         i-Pr                     CF.sub.3 MeO        n-Pr       OCF.sub.3 MeO         n-Pr                     CF.sub.3 MeO        CO.sub.2 Me                                                                              OCF.sub.3 MeO         CO.sub.2 Me              CF.sub.3 MeO        4-FPh      OCF.sub.3 MeO         4-FPh                    __________________________________________________________________________

                                      TABLE 8                                     __________________________________________________________________________     ##STR42##                                                                    R.sup.1  R.sup.2    R.sup.3    R.sup.1   R.sup.2     R.sup.3                  __________________________________________________________________________    CF.sub.3 F          CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3 F          4-FPh      OCF.sub.3 F           4-FPh                    CF.sub.3 Cl         CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3 Cl         4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3 Cl         n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3 Cl         i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3 OCH.sub.2 CF.sub.3                                                                       CO.sub.2 Me                                                                              OCF.sub.3 OCH.sub.2 CF.sub.3                                                                        CO.sub.2 Me              CF.sub.3 OCH.sub.2 CF.sub.3                                                                       4-FPh      OCF.sub.3 OCH.sub.2 CF.sub.3                                                                        4-FPh                    CF.sub.3 OCH.sub.2 CF.sub.3                                                                       n-Pr       OCF.sub.3 OCH.sub.2 CF.sub.3                                                                        n-Pr                     CF.sub.3 OCH.sub.2 CH.sub.3                                                                       i-Pr       OCF.sub.3 OCH.sub.2 CH.sub.3                                                                        i-Pr                     CF.sub.3 CF.sub.3   CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub.2 Me              __________________________________________________________________________

                                      TABLE 9                                     __________________________________________________________________________     ##STR43##                                                                    R.sup.1                                                                              R.sup.2                                                                             R.sup.3  Y        R.sup.1 R.sup.2                                                                             R.sup.3  Y                       __________________________________________________________________________    CF.sub.3                                                                             F     4-FPh    Me       OCF.sub.3                                                                             F     4-FPh    Me                      CF.sub.3                                                                             F     4-FPh    COMe     OCF.sub.3                                                                             F     4-FPh    COMe                    CF.sub.3                                                                             F     4-FPh    CO.sub.2 Me                                                                            OCF.sub.3                                                                             F     4-FPh    CO.sub.2 Me             CF.sub.3                                                                             F     CO.sub.2 Me                                                                            Me       OCF.sub.3                                                                             F     CO.sub.2 Me                                                                            Me                      CF.sub.3                                                                             F     CO.sub.2 Me                                                                            COMe     OCF.sub.3                                                                             F     CO.sub.2 Me                                                                            COMe                    CF.sub.3                                                                             F     CO.sub.2 Me                                                                            CO.sub.2 Me                                                                            OCF.sub.3                                                                             F     CO.sub.2 Me                                                                            CO.sub.2 Me             CF.sub.3                                                                             Cl    4-FPh    Me       OCF.sub.3                                                                             Cl    4-FPh    Me                      CF.sub.3                                                                             Cl    4-FPh    COMe     OCF.sub.3                                                                             Cl    4-FPh    COMe                    CF.sub.3                                                                             Cl    4-FPh    CO.sub.2 Me                                                                            OCF.sub.3                                                                             Cl    4-FPh    CO.sub.2 Me             CF.sub.3                                                                             Cl    CO.sub.2 Me                                                                            Me       OCF.sub.3                                                                             Cl    CO.sub.2 Me                                                                            Me                      CF.sub.3                                                                             Cl    CO.sub.2 Me                                                                            COMe     OCF.sub.3                                                                             Cl    CO.sub.2 Me                                                                            COMe                    CF.sub.3                                                                             Cl    CO.sub.2 Me                                                                            CO.sub.2 Me                                                                            OCF.sub.3                                                                             Cl    CO.sub.2 Me                                                                            CO.sub.2 Me             __________________________________________________________________________

                                      TABLE 10                                    __________________________________________________________________________     ##STR44##                                                                    R.sup.1  R.sup.2    R.sup.3    R.sup.1   R.sup.2     R.sup.3                  __________________________________________________________________________    CF.sub.3 F          n-Pr       OCF.sub.3 F           n-Pr                     CF.sub.3 F          i-Pr       OCF.sub.3 F           i-Pr                     CF.sub.3 F          CO.sub.2 Me                                                                              OCF.sub.3 F           CO.sub.2 Me              CF.sub.3 F          4-FPh      OCF.sub.3 F           4-FPh                    CF.sub.3 Cl         n-Pr       OCF.sub.3 Cl          n-Pr                     CF.sub.3 Cl         i-Pr       OCF.sub.3 Cl          i-Pr                     CF.sub.3 Cl         CO.sub.2 Me                                                                              OCF.sub.3 Cl          CO.sub.2 Me              CF.sub.3 Cl         4-FPh      OCF.sub.3 Cl          4-FPh                    CF.sub.3 OCH.sub.2 CF.sub.3                                                                       n-Pr       OCF.sub.3 OCH.sub.2 CF.sub.3                                                                        n-Pr                     CF.sub.3 OCH.sub.2 CF.sub.3                                                                       i-Pr       OCF.sub.3 OCH.sub.2 CF.sub.3                                                                        i-Pr                     CF.sub.3 OCH.sub.2 CF.sub.3                                                                       CO.sub. 2 Me                                                                             OCF.sub.3 OCH.sub.2 CF.sub.3                                                                        CO.sub.2 Me              CF.sub.3 OCH.sub.2 CF.sub.3                                                                       4-FPh      OCF.sub.3 OCH.sub.2 CF.sub.3                                                                        4-FPh                    CF.sub.3 CF.sub.3   CO.sub.2 Me                                                                              OCF.sub.3 CF.sub.3    CO.sub.2 Me              __________________________________________________________________________

                                      TABLE 11                                    __________________________________________________________________________     ##STR45##                                                                    E is H                         E is Me                                        R.sup.1  R.sup.2     R.sup.3   R.sup.1   R.sup.2    R.sup.3                   __________________________________________________________________________    CF.sub.3 F           n-Pr      CF.sub.3  F          n-Pr                      CF.sub.3 F           i-Pr      CF.sub.3  F          i-Pr                      CF.sub.3 F           CO.sub.2 Me                                                                             CF.sub.3  F          CO.sub.2 Me               CF.sub.3 F           4-FPh     CF.sub.3  F          4-FPh                     CF.sub.3 Cl          n-Pr      CF.sub.3  Cl         n-Pr                      CF.sub.3 Cl          i-Pr      CF.sub.3  Cl         i-Pr                      CF.sub.3 Cl          CO.sub.2 Me                                                                             CF.sub.3  Cl         CO.sub.2 Me               CF.sub.3 Cl          4-FPh     CF.sub.3  Cl         4-FPh                     CF.sub.3 OCH.sub.2 CF.sub.3                                                                        n-Pr      CF.sub.3  OCH.sub.2 CF.sub.3                                                                       n-Pr                      CF.sub.3 OCH.sub.2 CF.sub.3                                                                        i-Pr      CF.sub.3  OCH.sub. 2 CF.sub.3                                                                      i-Pr                      CF.sub.3 OCH.sub.2 CF.sub.3                                                                        CO.sub.2 Me                                                                             CF.sub.3  OCH.sub.2 CF.sub.3                                                                       CO.sub.2 Me               CF.sub.3 OCH.sub.2 CF.sub.3                                                                        4-FPh     CF.sub.3  OCH.sub.2 CF.sub.3                                                                       4-FPh                     CF.sub.3 CF.sub.3    4-FPh     CF.sub.3  CF.sub.3   4-FPh                     CF.sub.3 CF.sub.3    CO.sub.2 Me                                                                             CF.sub.3  CF.sub.3   CO.sub.2 Me               OCF.sub.3                                                                              F           n-Pr      OCF.sub.3 F          n-Pr                      OCF.sub.3                                                                              F           i-Pr      OCF.sub.3 F          i-Pr                      OCF.sub.3                                                                              F           CO.sub.2 Me                                                                             OCF.sub.3 F          CO.sub.2 Me               OCF.sub.3                                                                              F           4-FPh     OCF.sub.3 F          4-FPh                     OCF.sub.3                                                                              Cl          n-Pr      OCF.sub.3 Cl         n-Pr                      OCF.sub.3                                                                              Cl          i-Pr      OCF.sub.3 Cl         i-Pr                      OCF.sub.3                                                                              Cl          CO.sub.2 Me                                                                             OCF.sub.3 Cl         CO.sub.2 Me               OCF.sub.3                                                                              Cl          4-FPh     OCF.sub.3 Cl         4-FPh                     OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        n-Pr      OCF.sub.3 OCH.sub.2 CF.sub.3                                                                       n-Pr                      OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        i-Pr      OCF.sub.3 OCH.sub.2 CF.sub.3                                                                       i-Pr                      OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        CO.sub.2 Me                                                                             OCF.sub.3 OCH.sub.2 CF.sub.3                                                                       CO.sub.2 Me               OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        4-FPh     OCF.sub.3 OCH.sub.2 CF.sub.3                                                                       4-FPh                     OCF.sub.3                                                                              CF.sub.3    4-FPh     OCF.sub.3 CF.sub.3   4-FPh                     OCF.sub.3                                                                              CF.sub.3    CO.sub.2 Me                                                                             OCF.sub.3 CF.sub.3   CO.sub.2 Me               __________________________________________________________________________

                                      TABLE 12                                    __________________________________________________________________________     ##STR46##                                                                    R.sup.1  R.sup.2    R.sup.3    R.sup.1  R.sup.2     R.sup.3                   __________________________________________________________________________    CF.sub.3 F          n-Pr       OCF.sub.3                                                                              F           n-Pr                      CF.sub.3 F          i-Pr       OCF.sub.3                                                                              F           i-Pr                      CF.sub.3 F          Ph         OCF.sub.3                                                                              F           Ph                        CF.sub.3 F          4-FPh      OCF.sub.3                                                                              F           4-FPh                     CF.sub.3 Cl         n-Pr       OCF.sub.3                                                                              Cl          n-Pr                      CF.sub.3 Cl         i-Pr       OCF.sub.3                                                                              Cl          i-Pr                      CF.sub.3 Cl         Ph         OCF.sub.3                                                                              Cl          Ph                        CF.sub.3 Cl         4-FPh      OCF.sub.3                                                                              Cl          4-FPh                     CF.sub.3 CF.sub.3   n-Pr       OCF.sub.3                                                                              CF.sub.3    n-Pr                      CF.sub.3 CF.sub.3   i-Pr       OCF.sub.3                                                                              CF.sub.3    i-Pr                      CF.sub.3 CF.sub.3   Ph         OCF.sub.3                                                                              CF.sub.3    Ph                        CF.sub.3 CF.sub.3   4-FPh      OCF.sub.3                                                                              CF.sub.3    4-FPh                     CF.sub. 3                                                                              OCH.sub.2 CF.sub.3                                                                       n-Pr       OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        n-Pr                      CF.sub.3 OCH.sub.2 CF.sub.3                                                                       i-Pr       OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        i-Pr                      CF.sub.3 OCH.sub.2 CF.sub.3                                                                       Ph         OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        Ph                        CF.sub.3 OCH.sub.2 CF.sub.3                                                                       4-FPh      OCF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        4-FPh                     __________________________________________________________________________

Formulation and Use

The compounds of this invention will generally be used in formulationwith an agriculturally suitable carrier comprising a liquid or soliddiluent or an organic solvent. Useful formulations of the compounds ofFormulas I and II can be prepared in conventional ways. They includedusts, granules, baits, pellets, solutions, suspensions, emulsions,wettable powders, emulsifiable concentrates, dry flowables and the like.Many of these can be applied directly. Sprayable formulations can beextended in suitable media and used at spray volumes of from about oneto several hundred liters per hectare. High strength compositions areprimarily used as intermediates for further formulation. Theformulations, broadly, contain from less than about 1% to 99% by weightof active ingredient(s) and at least one of a) about 0.1% to 20%surfactant(s) and b) about 5% to 99% solid or liquid diluent(s). Morespecifically, they will contain effective amounts of these ingredientsin the following approximate proportions:

    ______________________________________                                                    Percent by Weight                                                             Active                                                                        Ingredient                                                                            Diluent(s)                                                                              Surfactants(s)                                  ______________________________________                                        Wettable Powders                                                                            25-90     0-74      1-10                                        Oil Suspensions,                                                                             5-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Dusts          1-25     70-99     0-5                                         Granules, Baits                                                                             0.01-95   5-99      0-15                                        and Pellets                                                                   High Strength 90-99     0-10      0-2                                         Compositions                                                                  ______________________________________                                    

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N. J. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide," 2nd Ed.,Interscience,. New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", Allured Publ. Corp., Ridgewood, N. J., as well asSisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ.Co., Inc., New York, 1964, list surfactants and recommended uses. Allformulations can contain minor amounts of additives to reduce foam,caking, corrosion, microbiological growth, etc. Preferably, ingredientsshould be approved by the U.S. Environmental Protection Agency for theuse intended.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example, U.S.Pat. No. 3,060,084). Granules and pellets can be made by spraying theactive material upon preformed granular carriers or by agglomerationtechniques. See J. E. Browning, "Agglomeration", Chemical Engineering,Dec. 4, 1967, pages 147 and following, and "Perry's Chemical Engineer'sHandbook", 4th Ed., McGraw-Hill, New York, 1963, pages 8 to 59 andfollowing.

Example A

Emulsifiable Concentrate

    ______________________________________                                        7-fluoro-,4a-(4-fluorophenyl)-3,4,4a,5-                                                              20%                                                    tetrahydro-N-[4-(trifluoromethyl)-                                            phenyl]-2H-indeno[1,2-c]-pyridazine-                                          2-carboxamide                                                                 blend of oil soluble sulfonates                                                                      10%                                                    and polyoxyethylene ethers                                                    isophorone             70%                                                    ______________________________________                                    

The ingredients are combined and stirred with gentle warming to speedsolution. A fine screen filter is included in packaging operation toinsure the absence of any extraneous undissolved material in theproduct.

Example B

Wettable Powder

    ______________________________________                                        7-fluoro-,4a-(4-fluorophenyl)-3,4,4a,5-                                                              30%                                                    tetrahydro-N-[4-(trifluoromethyl)-                                            phenyl]-2H-indeno]1,2-c]-pyridazine-                                          2-carboxamide                                                                 sodium alkylnaphthalenesulfonate                                                                      2%                                                    sodium ligninsulfonate  2%                                                    synthetic amorphous silica                                                                            3%                                                    kaolinite              63%                                                    ______________________________________                                    

The active ingredient is mixed with the inert materials in a blender.After grinding in a hammermill, the material is re-blended and siftedthrough a 50 mesh screen.

Example C

Dust

    ______________________________________                                        Wettable powder of Example B                                                                        10%                                                     pyrophyllite (powder) 90%                                                     ______________________________________                                    

The wettable powder and the pyrophyllite diluent are thoroughly blendedand then packaged. The product is suitable for use as a dust.

Example D

Granule

    ______________________________________                                        7-fluoro-,4a-(4-fluorophenyl)-3,4,4a,5-                                                              10%                                                    tetrahydro-N-[4-(trifluoromethyl)-                                            phenyl]2H-indeno[1,2-c]-pyridazine-                                           2-carboxamide                                                                 attapulgite granules (low volative                                                                   90%                                                    matter, 0.71/0.30 mm; U.S.S. No.                                              25-50 sieves)                                                                 ______________________________________                                    

The active ingredient is dissolved in a volatile solvent such as acetoneand sprayed upon dedusted and pre-warmed attapulgite granules in adouble cone blender. The acetone is then driven off by heating. Thegranules are then allowed to cool and are packaged.

Example E

Granule

    ______________________________________                                        Wettable powder of Example B                                                                        15%                                                     gypsum                69%                                                     potassium sulfate     16%                                                     ______________________________________                                    

The ingredients are blended in a rotating mixer and water sprayed on toaccomplish granulation. When most of the material has reached thedesired range of 0.1 to 0.42 mm (U.S.S. No. 18 to 40 sieves), thegranules are removed, dried, and screened. Oversize material is crushedto produce additional material in the desired range. These granulescontain 4.5% active ingredient.

Example F

Solution

    ______________________________________                                        7-fluoro-,4a-(4-fluorophenyl)-3,4,4a-5-                                                              25%                                                    tetrahydro-N-[4-(trifluoromethyl)-                                            phenyl]-2H-indeno[1,2-c]-pyridazine-                                          2-carboxamide                                                                 N-methyl-pyrrolidone   75%                                                    ______________________________________                                    

The ingredients are combined and stirred to produce a solution suitablefor direct, low volume application.

Example G

Aqueous Suspension

    ______________________________________                                        7-fluoro-,4a-(4-fluorophenyl)-3,4,4a,5-                                                              40%                                                    tetrahydro-N-[4-(trifluoromethyl)-                                            phenyl]-2H-indeno[1,2-c]-pyridazine-                                          2-carboxamide                                                                 polyacrylic acid thickener                                                                           0.3%                                                   dodecyclophenol polyethylene glycol                                                                  0.5%                                                   ether                                                                         disodium phosphate     1.0%                                                   monosodium phosphate   0.5%                                                   polyvinyl alcohol      1.0%                                                   water                  56.7%                                                  ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles substantially all under 5 microns in size.

Example H

Oil Suspension

    ______________________________________                                        7-fluoro-,4a-(4-fluorophenyl)-3,4,4a,5-                                                              35.0%                                                  tetrahydro-N-[4-(trifluoromethyl)-                                            phenyl]-2H-indeno[1,2-c]-pyridazine                                           2-carboxamide                                                                 blend of polyalcohol carboxylic                                                                      6.0%                                                   esters and oil soluble petroleum                                              sulfonates                                                                    xylene range solvent   59.0%                                                  ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles substantially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

Example I

Bait Granules

    ______________________________________                                        7-fluoro-,4a-(4-fluorophenyl)-3,4,4a,5-                                                              3.0%                                                   tetrahydro-N-[4-(trifluoromethyl)-                                            phenyl]-2H-indeno[1,2-c]-pyridazine-                                          2-carboxamide                                                                 blend of polyethoxylated nonyl-                                                                      9.0%                                                   phenols and sodium dodecyl-                                                   benzene sulfonates                                                            ground up corn cobs    88.0%                                                  ______________________________________                                    

The active ingredient and surfactant blend are dissolved in a suitablesolvent such as acetone and sprayed onto the ground corn cobs. Thegranules are then dried and packaged.

Compounds of Formulas I and II can also be mixed with one or more otherinsecticides, fungicides, nematocides, bactericides, acaricides, orother biologically active compounds to form a multi-component pesticidegiving an even broader spectrum of effective agricultural protection.Examples of other agricultural protectants with which compounds of thisinvention can be formulated are:

Insecticides:

3-hydroxy-N-methylcrotonamide(dimethylphosphate)ester (monocrotophos)

methylcarbamic acid, ester with 2,3-dihydro-2,2-dimethyl-7-benzofuranol(carbofuran)

O-[2,4,5-trichloro-α-(chloromethyl)benzyl]phosphoric acid,O',O'-dimethyl ester (tetrachlorvinphos)

2-mercaptosuccinic acid, diethyl ester, S-ester with thionophosphoricacid, dimethyl ester (malathion)

phosphorothioic acid, O,O-dimethyl, O-p-nitrophenyl ester (methylparathion)

methylcarbamic acid, ester with α-naphthol (carbaryl)

methyl O-(methylcarbamoyl)thiolacetohydroxamate (methomyl)

N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine (chlordimeform)

O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidylphosphorothioate(diazinon)

octachlorocamphene (toxaphene)

O-ethyl-O-p-nitrophenyl phenylphosphonothioate (EPN)

(S)-α-cyano-m-phenoxybenzyl(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate(deltamethrin)

Methyl-N',N'-dimethyl-N-[(methylcarbamoyl)oxy]-1-thioox amimidate(oxamyl)

cyano (3-phenoxyphenyl)-methyl-4-chloro-a-(1-methylethyl)benzeneacetate(fenvalerate)

(3-phenoxyphenyl)methyl(+)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin)

α-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (cypermethrin)

O-ethyl-S-(p-chlorophenyl)ethylphosphonodithioate (profenofos)

phosphorothiolothionic acid,

O-ethyl-O-[4-(methylthio)-phenyl]-S-n-propyl ester (sulprofos).

Additional insecticides are listed hereafter by their common names:triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb,acephate, azinphosmethyl, chlorpyrifos, dimethoate, fonophos,isofenphos, methidathion, methamidiphos, monocrotphos, phosmet,phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon,methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin,fluvalinate, flucythrinate, tralomethrin, metal- dehyde and rotenone.

Fungicides:

methyl 2-benzimidazolecarbamate (carbendazim)

tetramethylthiuram disulfide (thiuram)

n-dodecylguanidine acetate (dodine)

manganese ethylenebisdithiocarbamate (maneb)

1,4-dichloro-2,5-dimethoxybenzene (chloroneb)

methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl)

1-[2-(2,4-dichlorophenyl)-4-propyl-l,3-dioxolan-2ylmethyl]-1H-1,2,4-triazole(propiconazole)

2-cyano-N-ethylcarbamoyl-2-methoxyiminoacetamide (cymoxanil)

1-(4-chlorophenoxy)-3,3-dimethyl-l-(1H-1,2,4-triazol-1- yl)-2-butanone(triadimefon)

N-(trichloromethylthio)tetrahydrophthalimide (captan)

N-(trichloromethylthio)phthalimide (folpet)

1-[[[bis (4-fluorophenyl)][methyl]silyl]methyl]-1H-1,2,4-triazole.

Nematocides:

S-methyl 1-(dimethylcarbamoyl)-N-(methylcarbamoyloxy)thioformimidate

S-methyl 1-carbamoyl-N-(methylcarbamoyloxy)thioformimidate

N-isopropylphosphoramidic acid O-ethylO'-[4-(methylthio)-m-tolyl]diester (fenamiphos)

Bactericides:

tribasic copper sulfate

streptomycin sulfate

Acaricides:

senecioic acid, ester with 2-sec-butyl-4,6-dinitrophenol (binapacryl)

6-methyl-l,3-cithiolo[4,5-β]quinoxalin-2-one (oxythioquinox)

ethyl 4,4'-dichlorobenzilate (chlorobenzilate)

1,1-bis(p-chlorophenyl)-2,2,2-trichloroethanol (dicofol)

bis(pentachloro-2,4-cyclopentadien-1-yl) (dienochlor) tricyclohexyltinhydroxide (cyhexatin)

trans-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidine-3-carboxamide(hexythiazox)

amitraz

propargite

fenbutatin-oxide

Biological

Bacillus thuringiensis

Avermectin B.

Utility

The compounds of this invention exhibit activity against a wide spectrumof foliar and soil inhabiting arthropods which are pests of growing andstored agronomic crops, forestry, greenhouse crops, ornamentals, nurserycrops, stored food and fiber products, livestock, household, and publicand animal health. Those skilled in the art will recognize that not allcompounds are equally effective against all pests but the compounds ofthis invention display activity against economically importantagronomic, forestry, greenhouse, ornamental food and fiber product,stored product, domestic structure, and nursery pests, such as:

larvae of the order Lepidoptera including fall and beet armyworm andother Spodoptera spp., tobacco budworm, corn earworm and other Heliothisspp., European corn borer, navel orangeworm, stalk/stem borers and otherpyralids, cabbage and soybean loopers and other loopers, codling moth,grape berry moth and other tortricids, black cutworm, spotted cutworm,other cutworms and other noctuids, diamondback moth, green cloverworm,velvetbean caterpillar, green cloverworm, pink bollworm, gypsy moth, andspruce budworm: foliar feeding larvae and adults of the order Coleopteraincluding Colorado potato beetle, Mexican bean beetle, flea beetle,Japanese beetles, and other leaf beetles, boll weevil, rice waterweevil, granary weevil, rice weevil and other weevil pests, and soilinhabiting insects such as Western corn rootworm and other Diabroticaspp., Japanese beetle, European chafer and other coleopteran grubs, andwireworms;

adults and larvae of the orders Hemiptera and Homoptera includingtarnished plant bug and other plant bugs (miridae), aster leafhopper andother leafhoppers (cicadellidae), rice planthopper, brown planthopper,and other planthoppers (fulgoroidea), psylids, whiteflies (aleurodidae),aphids (aphidae), scales (coccidae and diaspididae), lace bugs(tingidae), stink bugs (pentatomidae), cinch bugs and other seed bugs(lyaaefdae), cicadas (cicadidae), spittlebugs (cercopids), squash bugs(coreidae), red bugs and cotton stainers (pyrrhocoridae);

adults and larvae of the order acari (mites) including European redmite, two spotted spider mite, rust mites, McDaniel mite, and foliarfeeding mites;

adults and immatures of the order Orthoptera including grasshoppers;

adults and immatures of the order Diptera including leafminers, midges,fruit flies (tephritidae), and soil maggots;

adults and immatures of the order Thysanoptera including onion thripsand other foliar feeding thrips.

The compounds are also active against economically important livestock,household, public and animal health pests such as:

insect pests of the order Hymenoptera including carpenter ants, bees,hornets, and wasps;

insect pests of the order Diptera including house flies, stable flies,face flies, horn flies, blow flies, and other muscoid fly pests, horseflies, deer flies and other Brachycera, mosquitoes, black flies, bitingmidges, sand flies, sciarids, and other Nematocera;

insect pests of the order Orthoptera including cockroaches and crickets;

insect pests of the order Isoptera including the Eastern subterraneantermite and other termites;

insect pests of the order Mallophaga and Anoplura including the headlouse, body louse, chicken head louse and other sucking and chewingparasitic lice that attack man and animals;

insect pests of the order Siphonoptera including the cat flea, dog fleaand other fleas.

The specific species for which control is exemplified are: fallarmyworm, Spodoptera fruigiperda; tobacco budworm, Hellothis virescens;boll weevil, Anthonomus grandis; aster leafhopper, Macrostelesfascifrons; black bean aphid, (Aphis Fabae); southern corn rootworm,Diabrotica undecimpunctata. The pest control protection afforded by thecompounds of the present invention is not limited, however, to thesespecies. The compounds of this invention may also be utilized asrodenticides.

Application

Arthropod pests are controlled and protection of agronomic crops, animaland human health is achieved by applying one or more of the Formula I orII compounds of this invention, in an effective amount, to theenvironment of the pests including the agronomic and/or nonagronomiclocus of infestation, to the area to be protected, or directly on thepests to be controlled. Because of the diversity of habitat and behaviorof these arthropod pest species, many different methods of applicationare employed. A preferred method of application is by spraying withequipment that distributes the compound in the environment of the pests,on the foliage, animal, person, or premise, in the soil or animal, tothe plant part that is infested or needs to be protected. Alternatively,granular formulations of these toxicant compounds can be applied to orincorporated into the soil. Other methods of application can also beemployed including direct and residual sprays, aerial sprays, baits,eartags, boluses, foggets, aerosols, and many others. The compounds canbe incorporated into baits that are consumed by the arthropods or indevices such as traps and the like which entice them to ingest orotherwise contact the compounds.

The compounds of this invention can be applied in their pure state, butmost often application will be of a formulation comprising one or morecompounds with suitable carriers, diluents, and surfactants and possiblyin combination with a food depending on the contemplated end use. Apreferred method of application involves spraying a water dispersion orrefined oil solution of the compounds. Combinations with spray oils,spray oil concentrations, and synergists such as piperonyl butoxideoften enhance the efficacy of the compounds of Formulae I and II.

The rate of application of the Formula I and II compounds required foreffective control will depend on such factors as the species ofarthropod to be controlled, the pest's life cycle, life stage, its size,location, time of year, host crop or animal, feeding behavior, matingbehavior, ambient moisture, temperature, etc. In general, applicationrates of 0.01 to 2 kg of active ingredient per hectare are sufficient toprovide large-scale effective control of pests in agronomic ecosystemsunder normal circumstances, but as little as 0.001 kg/hectare or as muchas 8 kg hectare may be required. For nonagronomic applications,effective use rates will range from about 1.0 to 50 mg/sguare meter butas little as about 0.1 mg/square meter or as much as 150 mg/square metermay be required.

The following Tests demonstrate the control efficacy of compounds ofFormulae I and II on specific pests; see Index Tables A, B, C and D forcompound descriptions.

                                      INDEX TABLE A                               __________________________________________________________________________     ##STR47##                                                                    CMPD   A        R.sup.1                                                                              R.sup.2    R.sup.3 Y R.sup.6 /R.sup.7                                                                         mp                     __________________________________________________________________________                                                           (°C.)            1     CH.sub.2 CF.sub.3                                                                             H          H       H H H        136-138                 2     CH.sub.2 CF.sub.3                                                                             7-F        4-FPh   H H H        224-227                 3     CH.sub.2 CH.sub.2                                                                      CF.sub.3                                                                             H          H       H H H        122-124                 4     CH.sub.2 CF.sub.3                                                                             7-F        H       H H H        126-164                 5     CH.sub.2 OCF.sub.3                                                                            7-OMe      4-FPh   H H H        150-152                 6     CH.sub.2 CF.sub.3                                                                             H          CO.sub.2 Me                                                                           H H H        188-191                 7     CH.sub.2 OCF.sub.3                                                                            7-F        4-FPh   H H H        216-218                 8     CH.sub.2 CF.sub.3                                                                             H          Ph      H H H        222-223                 9     CH.sub.2 CF.sub.3                                                                             7-F        CO.sub.2 Me                                                                           H H H        212-215                10     CH.sub.2 CF.sub.3                                                                             7-Cl       4-ClPh  H H H        135-138                11     CH.sub.2 OCF.sub.3                                                                            7-Cl       CO.sub.2 Me                                                                           H H H        196-198                12     CH.sub.2 OCF.sub.3                                                                            7-OCH.sub.2 CF.sub.3                                                                     CO.sub.2 Me                                                                           H H H        170-171                13     CH.sub.2 Cl     7-Cl       CO.sub.2 Me                                                                           H H H        185-186                14     CH.sub.2 Br     7-Cl       CO.sub.2 Me                                                                           H H H        196-197                15     CH.sub.2 OCF.sub.3                                                                            7-F        CO.sub.2 Me                                                                           H H H        173-174                16     CH.sub.2 CF.sub.3                                                                             7-OCH.sub.2 CF.sub.3                                                                     CO.sub.2 Me                                                                           H H H        218-219                17     CH.sub.2 Br     7-OCH.sub.2 CF.sub.3                                                                     CO.sub.2 Me                                                                           H H H        189-190                18     CH.sub.2 CF.sub.3                                                                             6-Cl       CO.sub.2 Me                                                                           H H H        233-235                19     CH.sub.2 OCH.sub.3                                                                            6-Cl       CO.sub.2 Me                                                                           H H H        190-191                20     CH.sub.2 OCF.sub.3                                                                            7-Cl       CO.sub. 2 Me                                                                          H O          172-176                21     CH.sub.2 CF.sub.3                                                                             7-OCH.sub.2 CF.sub.3                                                                     4-FPh   H H H        218                    22     CH.sub.2 CF.sub.3                                                                             7-F        Et      H H H        154-155                23     CH.sub.2 Br     7-F        Et      H H H        124-125                24     CH.sub.2 CF.sub.3                                                                             7-F        Me      H H H        172                    25     CH.sub.2 Cl     7-F        Et      H H H        128-130                26     CH.sub.2 OCF.sub.3                                                                            7-F        Et      H H H        115-118                27     CH.sub.2 CF.sub.3                                                                             7-OCH.sub.2 CF.sub.3                                                                     Et      H H H        169-173                28     CH.sub.2 Br     7-F        Me      H H H        150-151                29     CH.sub.2 CF.sub.3                                                                             7-F        n-Pr    H H H        210-218                30     CH.sub.2 CF.sub.3                                                                             7-OCH.sub.2 CF.sub.3                                                                     Me      H H H        179-180                31     CH.sub.2 Br     7-OCH.sub.2 CF.sub.3                                                                     Me      H H H        163-164                32     CH.sub.2 Br     7-F        n-Pr    H H H        190-192                33     CH.sub.2 OCF.sub.3                                                                            7-F        Me      H H H        148-149                34     CH.sub.2 Br     7-F        i-Pr    H H H        190-193                35     CH.sub.2 CF.sub.3                                                                             7-F        i-Pr    H H H        214-215                36     CH.sub.2 OCF.sub.3                                                                            7-F        n-Pr    H H H        194-195                37     CH.sub.2 CF.sub.3                                                                             7-OCH.sub.2 CF.sub.3                                                                     n-Pr    H H H        167-168                38     CH.sub.2 Br     7-OCH.sub.2 CF.sub.3                                                                     n-Pr    H H H        118-120                39     CH.sub.2 OCF.sub.3                                                                            7-OCH.sub.2 CF.sub.3                                                                     n-Pr    H H H        123-135                40     CH.sub.2 OCF.sub.3                                                                            7-F        Me      H H H        119-120                41     CH.sub.2 OCF.sub.3                                                                            7-F        i-Pr    H H H        189-190                42     CH.sub.2 OCF.sub.3                                                                            7-OCH.sub.2 CF.sub.3                                                                     Et      H H H        105-107                43     CH.sub.2 OCF.sub.3                                                                            7-OCH.sub.2 CF.sub.3                                                                     4-FPh   H H H        192-195                44     CH.sub.2 Br     7-OCH.sub.2 CF.sub.3                                                                     Et      H H H        151-153                45     CH.sub.2 CF.sub.3                                                                             7-OCH.sub.2 CF.sub.3                                                                     i-Pr    H H H        130-132                46     CH.sub.2 Br     7-OCH.sub.2 CF.sub.3                                                                     i-Pr    H H H        158-160                47     CH.sub.2 OCF.sub.3                                                                            7-OCH.sub.2 CF.sub.3                                                                     i-Pr    H H H         92-95                 48     CH.sub.2 Br     7-OCH.sub.2 CF.sub.3                                                                     4-FPh   H H H        165-167                49     CH.sub.2 CF.sub.3                                                                             7-Cl       Me      H H H        190-192                50     CH.sub.2 Br     7-Cl       Me      H H H        156-159                51     CH.sub.2 OCH.sub.3                                                                            7-Cl       Me      H H H        156-159                52     CH.sub.2 CF.sub.3                                                                             7-Cl       i-Pr    H H H        180-183                53     CH.sub.2 Br     7-Cl       i-Pr    H H H        165-168                54     CH.sub.2 CF.sub.3                                                                             7-OMe      Me      H H H        155-157                55     CH.sub.2 OCF.sub.3                                                                            7-OMe      Me      H H H        140-144                56     CH.sub.2 CF.sub.3                                                                             7-OMe      CO.sub.2 Me                                                                           H H H        181-190                57     CH.sub.2 Br     7-OMe      CO.sub.2 Me                                                                           H H H        169-170                58     CH.sub.2 OCF.sub.3                                                                            7-OMe      CO.sub.2 Me                                                                           H H H        160-162                59     CH.sub.2 CF.sub.3                                                                             7-Cl       CO.sub.2 Me                                                                           H H H        218-220                60     CH.sub.2 OCF.sub.3                                                                            7-CF3      CO.sub.2 Me                                                                           H H H        108-111                __________________________________________________________________________

                                      INDEX TABLE B                               __________________________________________________________________________     ##STR48##                                                                    CMPD    R.sup.1 R.sup.2                                                                              R.sup.3    E     Y  R.sup.6 /R.sup.7                                                                         mp                      __________________________________________________________________________                                                          (°C.)             61     CF.sub.3                                                                              H      H          H     H  H H        141-143                  62     Cl      H      H          H     H  H H        130-132                  63     OMe     H      H          H     H  H H         97-99                   64     CF.sub.3                                                                              4-Cl   H          H     H  H H        141-142                  65     Cl      4-Cl   H          H     H  H H        152-153                  66     CF.sub.3                                                                              H      CO.sub.2 Me                                                                              H     H  H H        127-129                  67     CF.sub.3                                                                              4-Cl   Me         H     H  H H        118-120                  68     CF.sub.3                                                                              4-Cl   CO.sub.2 Me                                                                              Me    H  H H        146-147.5                69     CF.sub.3                                                                              4-Cl   CO.sub.2 Me                                                                              Me    H  H H        oil                      70     CF.sub.3                                                                              H      CO.sub.2 Me                                                                              Me    H  H H        wax                      71     CF.sub.3                                                                              4-F    H          H     H  H H        134-135                  72     Cl      4-F    H          H     H  H H        153-154                  73     CF.sub.3                                                                              4-F    CO.sub.2 Me                                                                              H     H  H H        157-159                  74     CF.sub.3                                                                              H      Ph         H     H  H H        171-173                  75     CF.sub.3                                                                              4-Cl   4-ClPh     H     H  H H        144-149                  76     OCF.sub.3                                                                             4-Cl   4-ClPh     H     H  H H        135-139                  77     CF.sub.3                                                                              H      4-FPh      H     H  H H        173-175                  78     CF.sub.3                                                                              H      4-ClPh     H     H  H H        163-165                  79     OCF.sub.3                                                                             H      4-ClPh     H     H  H H        119-121                  80     CF.sub.3                                                                              4-F    4-FPh      H     H  H H        177-179                  81     CF.sub.3                                                                              H      Ph         H     H  O          164-166                  82     CF.sub.3                                                                              4-Cl   4-ClPh     H     H  O          165-168                  83     CF.sub.3                                                                              H      4-FPh      H     H  O          220-224                  84     CF.sub.3                                                                              H      4-ClPh     H     H  O          155-159                  85     CF.sub.3                                                                              4-F    4-FPh      H     H  O          190-200                  86     CF.sub.3                                                                              4-Cl   Ph         H     H  O          174-177                  87     CF.sub.3                                                                              4-Cl   Ph         H     H  H H        183-185                  88     OCF.sub.3                                                                             4-Cl   Ph         H     H  H H        172-175                  89     OCF.sub.3                                                                             4-CF.sub.3                                                                           Ph         H     H  H H        160-162                  90     CF.sub.3                                                                              3-Cl   Ph         H     H  H H        170-172                  91     OCF.sub.3                                                                             3-Cl   Ph         H     H  H H        150-152                  92     CF.sub.3                                                                              4-CF.sub.3                                                                           Ph         H     H  H H        164-166                  93     OCF.sub.3                                                                             3-F    Ph         H     H  H H        160-162                  94     CF.sub.3                                                                              3-F    Ph         H     H  H H        147-149                  95     CF.sub.3                                                                              3-Cl   Ph         H     H  O          178-180                  96     CF.sub.3                                                                              H      4-FPh      H     Ac H H        oil                      97     CF.sub.3                                                                              H      4-FPh      H     Me H H        125-127                  98     OCF.sub.3                                                                             3-Cl   Ph         H     H  O          oil                      99     CF.sub.3                                                                              3-CF.sub.3                                                                           Ph         H     H  H H        154-156                 100     OCF.sub.3                                                                             3-CF.sub.3                                                                           Ph         H     H  H H        133-135                 101     CF.sub.3                                                                              H      4-FPh      H     H  H H        CO.sub.2 Me             102     CF.sub.3                                                                              H      i-Pr       H     H  H H         88-90.5                103     CF.sub.3                                                                              H      CH.sub.2 CHCH.sub.2                                                                      H     H  H H         98-100                 104     CF.sub.3                                                                              H      Et         H     H  H H         72-75                  __________________________________________________________________________

                  INDEX TABLE C                                                   ______________________________________                                         ##STR49##                                                                    CMPD   R.sup.1 R.sup.2  R.sup.3                                                                            E    Y      mp (°C.)                      ______________________________________                                        105    CF.sub.3                                                                              3-Cl     4-F  H    H      132-134                              106    OCF.sub.3                                                                             3-Cl     4-F  H    H      120-122                              107    CF.sub.3                                                                              4-Cl     H    H    H      129-130                              108    CF.sub.3                                                                              2-F      H    H    H      174-175                              109    OCF.sub.3                                                                             2-F      H    H    H      104-105                              110    OCF.sub.3                                                                             4-Cl     H    H    H      141-142                              111    Br      4-Cl     H    H    H      198-199                              112    OCF.sub.3                                                                             3-Br     4-F  H    H      145-146                              113    CF.sub.3                                                                              3-Cl     4-F  Me   H      153-155                              114    OCF.sub.3                                                                             3-Cl     4-F  Me   H      138-140                              115    Br      3-Cl     4-F  Me   H      150-151                              116    CF.sub.3                                                                              3-F      H    H    H      169-170                              117    CF.sub.3                                                                              3-Cl     4-Cl H    H      138-140                              118    OCF.sub.3                                                                             3-Cl     4-Cl H    H      139-140                              119    Br      3-Cl     4-Cl H    H      149-150                              120    CF.sub.3                                                                              3-F      3-Cl H    H      196-197                              121    OCF.sub.3                                                                             3-F      3-Cl H    H      158-160                              122    CF.sub.3                                                                              2-Cl     H    H    H      159-160                              123    Br      2-Cl     H    H    H      158-159                              124    Cl      2-Cl     H    H    H      143-144                              125    CF.sub.3                                                                              3-F      4-F  Me   H      164-165                              126    OCF.sub.3                                                                             3-F      4-F  Me   H      150-151                              127    CF.sub.3                                                                              3-Cl     H    H    H      183-184                              128    OCF.sub.3                                                                             3-Cl     H    H    H      174-175                              129    OCF.sub.3                                                                             4-Br     4-Cl H    H      120-122                              130    OCF.sub.3                                                                             3-CF.sub.3                                                                             H    H    H      153-154                              131    CF.sub.3                                                                              3-Br     4-Cl H    H      164-165                              132    Br      3-Br     4-Cl H    H      159-160                              133    CF.sub.3                                                                              3-F      4-Cl H    H      135-136                              134    OCF.sub.3                                                                             3-F      4-Cl H    H      134-135                              135    OCF.sub.3                                                                             3-CF.sub.3                                                                             H    H    CO.sub.2 Me                                                                          120-122                              136    OCF.sub.3                                                                             3-CF.sub.3                                                                             4-F  H    H      160-161                              137    Br      3-CF.sub.3                                                                             4-F  H    H      167-168                              138    OCF.sub.3                                                                             3-NO.sub.2                                                                             H    H    H      177-178                              139    Br      3-NO.sub.2                                                                             H    H    H      162-163                              140    OCF.sub.3                                                                             3-F      H    H    H      163-164                              141    OCH.sub.3                                                                             3-Cl     4-Cl H    H      90-92                                142    OCF.sub.3                                                                             3-NO.sub.2                                                                             4-F  H    H      171-174                              143    OCF.sub.3                                                                             3-OCH.sub.3                                                                            H    H    H      156-157                              144    OCF.sub.3                                                                             H        4-F  H    H      131-132                              145    CF.sub.3                                                                              H        4-F  H    H      168-169                              146    Br      H        4-F  H    H      178-179                              147    OCF.sub.3                                                                             3-CF.sub.3                                                                             4-Cl H    H      118-119                              148    CF.sub.3                                                                              3-CF.sub.3                                                                             4-Cl H    H      139-140                              149    OCF.sub.3                                                                             3-CF.sub.3                                                                             4-Br H    H      122-124                              150    OCF.sub.3                                                                             3-Cl     4-Me H    H      138-140                              151    Br      3-Cl     4-Me H    H      147-148                              152    CF.sub.3                                                                              3-Cl     4-Me H    H      144-145                              153    CF.sub.3                                                                              3-Br     4-Br H    H      155-156                              154    OCF.sub.3                                                                             3-Br     4-Br H    H      133-134                              155    Br      3-Br     4-Br H    H      98-99                                156    CF.sub.3                                                                              3-F      4-Me H    h      180-181                              157    OCF.sub.3                                                                             3-F      4-Me H    H      144-145                              158    Br      3-F      4-Me H    H      166-167                              ______________________________________                                    

                  INDEX TABLE D                                                   ______________________________________                                         ##STR50##                                                                    CMPD    A         R.sup.1 R.sup.2                                                                             R.sup.3                                                                            mp (°C.)                          ______________________________________                                        159     OCH.sub.2 OCF.sub.3                                                                             H     Me   142-143                                  ______________________________________                                    

TEST A Fall Armyworm

Test units, each consisting of an 8-ounce (230 mL) plastic cupcontaining a layer of wheat germ diet, approximately 0.5 cm thick, wereprepared. Ten third-instar larvae of fall armyworm (Spodopterafrugiperda) were placed into each cup. Solutions of each of the testcompounds (acetone/distilled water 75/25 solvent) were sprayed into thecups, a single solution per set of three cups. Spraying was accomplishedby passing the cups, on a conveyer belt, directly beneath a flat fanhydraulic nozzle which discharged the spray at a rate of 0.5 pounds ofactive ingredient per acre (about 0.55 kg/ha) at 30 p.s.i. (207 kPa).The cups were then covered and held at 27° C. and 50% relative humidityfor 72 hours, after which time readings were taken. Of the compoundstested, the following resulted in greater than or equal to 80%mortality: 1, 2, 4, 6, 8, 13, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24,25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42,43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59,60**, 66, 74, 75, 76, 78, 83, 88, 89, 90, 91, 92, 95, 96, 97, 98, 99,100, 101, 105*, 106*, 109, 112, 116*, 117, 118, 119, 120, 121, 122*,123*, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139,141, 142, 143, 144, 145, 146, 147, 148*, 149, 150, 151, 152, 153, 154,155, 156 and 157.

TEST B Tobacco Budworm

The test procedure of Test 1 was repeated for efficacy againstthird-instar larvae of the tobacco budworm (Hellothis virescens) exceptthat mortality was assessed at 48 hours. Of the compounds tested, thefollowing resulted in greater than or equal to 80% mortality: 2, 6, 13,14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31,32, 34, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52,53, 55, 56, 58, 59, 60**, 77, 78, 89, 91, 96, 97, 98, 99, 100, 101, 105,106, 112, 117, 118, 119, 128, 129, 130, 131, 132, 133, 134, 135, 136,137, 138, 142, 144, 145, 147, 148, 149, 150, 151, 152, 153, 154, 155 and157.

TEST C Southern Corn Rootworm

Test units, each consisting of an 8-ounce (230 mL) plastic cupcontaining 1 sprouted corn seed, were prepared. Sets of three test unitswere sprayed as described in Test A with individual solutions of thetest compounds. After the spray on the cups had dried, five third-instarlarvae of the southern corn rootworm (Diabrotica undecimpunctatahowardi) were placed into each cup. A moistened dental wick was insertedinto each cup to prevent drying and the cups were then covered. The cupswere then held at 27° C. and 50% relative humidity for 48 hours, afterwhich time mortality readings were taken. Of the compounds tested, thefollowing resulted in greater than or equal to 80% mortality: 1, 2, 4,6, 8, 13, 14, 15, 16, 17, 18, 19, 22, 23, 24, 25, 26, 27, 28, 29, 30,31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 46, 47, 48, 49,50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60**, 66, 74, 77, 78, 83, 89,91, 92, 95, 96, 97, 98, 99, 100, 101, 105, 106, 107, 112, 116, 118, 127,128, 129, 130, 134, 136, 137, 138, 139, 142, 144, 145, 146, 147 and 159.

TEST D Aster Leafhopper

Test units were prepared from a series of 12-ounce (350 mL) cups, eachcontaining oat (Avena sativa) seedlings in a 1-inch (2.54 cm) layer ofsterilized soil. The test units were sprayed as described in Test A withindividual solutions of the below-listed compounds. After the oats haddried from the spraying, between 10 and 15 adult aster leafhoppers(Mascrosteles fascifrons) were aspirated into each of the covered cups.The cups were held at 27° C. and 50% relative humidity for 48 hours,after which time mortality readings were taken. Of the compounds tested,the following resulted in greater than or equal to 80% mortality: 2, 13,14, 15, 19, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36,38, 39, 40, 41, 42, 44, 45, 46, 47, 49, 50, 51, 52, 59, 60**, 66, 74,77, 78, 89, 90, 96, 100, 101, 105, 106, 130, 144, 145, 147, 148 and 149.

TEST E Boll Weevil

Five adult boll weevils (Anthonomus grandis grandis) were placed intoeach of a series of 9 ounce (260 mL) cups. The test procedure employedwas then otherwise the same as in Test A with three cups per treatment.Mortality readings were taken 48 hours after treatment. Of the compoundstested, the following resulted in greater than or equal to 80%mortality: 1, 2, 4, 6, 8, 13, 14, 15, 16, 17, 18, 19, 22, 24, 25, 26,29, 30, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47,48, 49, 50, 51, 52, 53, 55, 56, 57, 58, 59, 60**, 70, 74, 77, 78, 89,90, 91, 92, 95, 96, 97, 98, 99, 100, 105, 112, 127, 130, 131, 134, 135,137, 138, 139, 141, 142, 144 and 145.

What is claimed is:
 1. A compound selected from groups having Formulae Iand II: ##STR51## wherein: Q is selected from the group ##STR52## A andE are taken together to form V; V is selected from the group --CH₂ --,--CH₂ CH₂ --, --O--, --S--, --SO--, --SO₂ --, --NR¹¹ --, --OCH₂ --,--SCH₂ --, --N(R¹¹)CH₂ --, substituted --CH₂ --, and substituted --CH₂CH₂ --, the substituents independently selected from 1-2 halogen and 1-2methyl; provided that when V is --OCH₂ --, --SCH₂ -- or --N(R¹¹)CH₂ --,either atom can be attached to the aromatic moiety;G is selected fromthe group ##STR53## X is selected from the group O, S and N-X² ; X¹ isselected from the group Cl, Br, OR¹², SR¹² and NR¹² R¹³ ; X² is selectedfrom the group R¹², OH, OR¹², CN, SO₂ R¹², SO₂ Ph, OC(O)NR¹³ R¹⁴,OC(O)OR¹², NR¹³ R¹⁴ and phenyl optionally subtituted with R¹⁵ ; Y isselected from the group H, C₁ -C₆ alkyl, benzyl optionally substitutedby W, C₂ -C₆ alkoxyalkyl, CHO, C₂ -C₆ alkylcarbonyl, C₂ -C₆alkoxycarbonyl, C₂ -C₆ haloalkylcarbonyl, C₁ -C₆ alkylthio, C₁ -C₆haloalkylthio, phenylthio, R¹⁶ OC(O)NR¹⁷ S-- and R¹⁸ (R¹⁹)NS--; R¹ andR² are independently selected from the group H, C₁ -C₆ alkyl, C₁ -C₆haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃ -C₆haloalkynyl, C₂ -C₆ alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆nitroalkyl, C₂ -C₆ cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆cycloalkyl, C₃ -C₆ halocycloalkyl, phenyl optionally substituted with 1to 3 substituents independently selected from W, benzyl optionallysubstituted with 1 to 3 substituents independently selected from W,halogen, CN, N₃, SCN, NO₂, OR²¹, SR²¹, S(O)R²¹, S(O)₂ R²¹, OC(O)R²¹,OS(O)₂ R²¹, CO₂ R²¹, C(O)R²¹, C(O)NR²¹ R²², SO₂ NR²¹ R²², NR²¹ R²² ,NR²² C(O)R²¹, OC(O)NHR²¹, NR²² C(O)NHR²¹ and NR²² SO₂ R²¹ ; or when m, nor p is 2, (R¹)₂ when attached to adjacent atoms can be taken together,or (R²)₂ when attached to adjacent atoms can be taken together, or(R²⁰)₂ when attached to adjacent atoms can be taken together as --OCH₂O--, --OCF₂ O--, --OCH₂ CH₂ O--, --CH₂ C(CH₃)₂ O--, --CF₂ CF₂ O-- or--OCF₂ CF₂ O-- to form a cyclic bridge; provided that when R¹, R² or R²⁰is S(O)R²¹, S(O)₂ R²¹, OC(O)R²¹ or OS(O)₂ R²¹ then R²¹ is other than H;R³ is selected from the group H, J, N₃, NO₂, halogen, N(R²⁶)R²⁷, C₁ -C₆alkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₂ -C₆alkoxyalkyl, C₃ -C₈ alkoxycarbonylalkyl, CO₂ R²¹, OR²³, C(O)R²¹,C(O)NR²¹ R²², C(S)NR²¹ R²², C(S)R²¹, C(S)SR²¹, CN, Si(R³²)(R³³)R³¹,S(O)R³¹, SO₂ R³¹, --P(O) (OR³¹)₂, phenyl, phenyl substituted by(R²⁰)_(p), benzyl and benzyl substituted with 1 to 3 substituentsindependently selected from W; or R³ is C₂ -C₆ epoxyalkyl optionallysubstituted with a group selected from C₁ -C₃ alkyl, CN, C(O)R²⁸, CO₂R²⁸, and phenyl optionally substituted with W, or R³ is C₁ -C₆ alkylsubstituted with a group selected from C(O)N(R²⁹)R³⁰, C(O)R²⁹, SR³¹,S(O)R³¹, SO₂ R³¹, SCN, halogen, CN, C₁ -C₂ haloalkoxy, Si(R³²)(R³³)R³¹,N(R²⁶)R²⁷, NO₂, OC(O)R²⁹ and J; J is selected from the group consistingof ##STR54## R⁴ is selected from the group H, halogen, C₁ -C₆ alkyl, CO₂R²⁴, phenyl, pyridinyl and phenyl or pyridinyl substituted with Cl, Br,F, CF₃, NO₂, OCF₃, OCF₂ H or CN; R⁵ and R⁷ are independently selectedfrom the group H and C₁ -C₂ alkyl; R⁶ is selected from the group H, C₁-C₆ alkyl, CO₂ R²⁴, and optionally substituted phenyl and pyridinyl,wherein the substituents are selected from Cl, Br, F, CF₃, NO₂, OCF₃,OCF₂ H or CN; R⁴ and R⁵ can be taken together to form ═0; R⁶ and R⁷ canbe taken together to form ═0; R⁸ is selected from the group H and C₁ -C₂alkyl; R⁹ is selected from the group H, C₁ -C₂ alkyl and C₁ -C₂alkylcarbonyl; R¹⁰ is selected from the group H , C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₂ -C₄ alkylcarbonyl C₂ -C₄ haloalkylcarbonyl, C₂ -C₄alkoxycarbonyl C₂ -C₄ haloalkoxycarbonyl, C₂ -C₅ alkylaminocarbonyl, C₃-C₆ cycloalkyl, C₃ -C₆ halocycloalkyl, C₄ -C₇ alkylcycloalkyl, C₄ -C₇haloalkylcycloalkyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl andSO₂ Ph optionally substituted with Cl, Br or CH₃ ; R¹¹ is selected fromthe group H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkenyl, C₂ -C₄haloalkenyl, SR²¹, S(O)R²¹, S(O)₂ R²¹, C(O)R²¹, CO₂ R²¹, C(O)NR²¹ R²⁵,C(S)NR²¹ R²⁵, C(S)R²¹, C(S)OR²¹, P(O)(OR²¹)₂, P(S)(OR²¹)₂,P(O)(R²¹)OR²¹, P(O)(R²¹)SR²⁵, and optionally substituted phenyl andbenzyl wherein the substituents(s) are selected from F, Cl, Br, CH₃, CF₃or OCF₃ ; provided that when R¹¹ is other than C(O)R²¹, C(O)NR²¹ R²⁵ orC(S)NR²¹ R²⁵ then R²¹ is other than H; R¹² is selected from the group C₁-C₃ alkyl, benzyl optionally substituted with R¹⁵, C₂ -C₄ alkenyl, C₂-C₄ alkynyl, C₁ -C₃ haloalkyl, C₂ -C₄ haloalkenyl, C₃ -C₆ cycloalkyl andC₁ -C₃ alkyl substituted with OCH₃ , OCH₂ CH₃, NO₂, CN, CO₂ CH₃, CO₂ CH₂CH₃ , SCH₃ or SCH₂ CH₃ ; R¹³ is selected from the group H, C₁ -C₄ alkylC₁ -C₄ haloalkyl, C₂ -C₄ alkoxycarbonyl, and optionally substitutedphenyl and pyridinyl wherein the substituents(s) are selected fromR^(15;) or R¹² and R¹³ can be taken together to form --(CH₂)₄ --,--(CH₂)₅ -- or --CH₂ CH₂ OCH₂ CH₂ -- each of which is optionallysubstituted with 1 or 2 CH₃ groups; R¹⁴ is selected from the group H andC₁ -C₄ alkyl; or R¹³ and R¹⁴ can be taken together to form --(CH₂)₄ --,--(CH₂)₅ -- or CH₂ CH₂ OCH₂ CH₂ each of which is optionally substitutedwith 1 or 2 CH₃ groups; R¹⁵ is selected from the group halogen, CN, C₁-C₃ haloalkyl and C₁ -C₃ haloalkoxy; R¹⁶ is C₁ -C₆ alkyl; R¹⁷ is C₁ -C₄alkyl; R¹⁸ and R¹⁹ are independently C₁ -C₄ alkyl; or R¹⁸ and R¹⁹ can betaken together as --CH₂ CH₂ CH₂ CH₂ CH₂ -- or --CH₂ CH₂ OCH₂ CH₂ --; R²⁰is selected from the group C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃ -C₆ haloalkynyl, C₂ -C₆alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆ nitroalkyl, C₂ -C₆cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆ cycloalkyl, C₃ -C₆halocycloalkyl, phenyl optionally substituted with 1 to 3 substituentsindependently selected from W, benzyl optionally substituted with 1 to 3substituents independently selected from W, halogen, CN, N₃, SCN, NO₂,OR²¹, SR²¹, S(O)R²¹, S(O)₂ R²¹, OC(O)R²¹, OS(O)₂ R²¹, CO₂ R²¹, C(O)R²¹,C(O)NR²¹ R²², SO₂ NR²¹ R²², NR²¹ R²², NR²² C(O)R²¹, OC(O)NHR²¹, NR²²C(O)NHR²¹ and NR²² SO₂ R²¹ ; or when m, n or p is 2, (R¹)₂ when attachedto adjacent atoms can be taken together, or (R²)₂ when attached toadjacent atoms can be taken together, or (R²⁰)₂ when attached toadjacent atoms can be taken together as --OCH₂ O--, --OCF₂ O--, --OCH₂CH₂ O--, --CH₂ C(CH₃)₂ O--, CF₂ CF₂ O-- or --OCF₂ CF₂ O-- to form acyclic bridge; provided that when R¹, R² or R²⁰ is S(O)R²¹, S(O)₂ R²¹,OC(O)R²¹ or OS(O)₂ R²¹ then R²¹ is other than H; R²¹ is selected fromthe group H, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆haloalkenyl, C₂ -C₆ alkynyl, C₃ -C₆ haloalkynyl, C₂ -C₆ alkoxyalkyl, C₂-C₆ alkylthioalkyl, C₁ -C₆ nitroalkyl, C₂ -C₆ cyanoalkyl, C₃ -C₈alkoxycarbonylalkyl, C₃ -C₆ cycloalkyl, C₃ -C₆ halocycloalkyl, andoptionally substituted phenyl and benzyl wherein the substituents are 1to 3 substituents independently selected from W; R²² is selected fromthe group H and C₁ -C₄ alkyl; or R²¹ and R²², when attached to the sameatom, can be taken together as --(CH₂)₄ --, --(CH₂)₅ --, or --CH₂ CH₂OCH₂ CH₂ --; R²³ is selected from the group H, C₁ -C₄ alkyl, C₂ -C₄alkenyl, C₂ -C₄ alkynyl, C₂ -C₄ alkylcarbonyl, C₂ -C₄ alkoxycarbonyl andC₁ -C₄ alkylsulfonyl; R²⁴ is C₁ -C₃ alkyl; R²⁵ is selected from thegroup H, C₁ -C₄ alkyl, C₂ -C₄ alkenyl and C₂ -C₄ alkynyl; R²⁶ isselected from the group H, C(O)C₁ -C₆ alkyl, CO₂ C₁ -C₆ alkyl,optionally substituted C₁ -C₄ alkyl, optionally substituted C₂ -C₄alkenyl, and optionally substituted C₂ -C₄ alkynyl, the substituentsselected from C₁ -C₂ alkoxy, CN, C(O)R³⁴ and CO₂ R³¹ ; R²⁷ is selectedfrom the group H, C₁ -C₃ alkyl, phenyl, phenyl substituted with W,benzyl and benzyl substituted with W; R²⁸ is selected from the group H,C₁ -C₄ alkyl, C₂ -C₄ alkenyl and C₂ -C₄ alkynyl; R²⁹ and R³⁰ areindependently selected from the group H and C₁ -C₂ alkyl; R³¹ isselected from the group C₁ -C₃ alkyl, phenyl and phenyl substituted withW; R³² is C₁ -C₃ alkyl; R³³ is C₁ -C₃ alkyl; R³⁴ is selected from thegroup H, C₁ -C₃ alkyl, phenyl and phenyl substituted by W; W is selectedfrom the group halogen, CN, NO₂, C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, C₁ -C₂alkoxy, C₁ -C₂ haloalkoxy, C₁ -C₂ alkylthio, C₁ -C₂ haloalkylthio, C₁-C₂ alkylsulfonyl and C₁ -C₂ haloalkylsulfonyl; m is 1 to 3; n is 1 to3; p is 1 to 3; u is 1 or 2; and Z is C or N.
 2. A compound according toclaim 1 wherein:R¹ is selected from the group H, C₁ -C₆ alkyl, C₂ -C₆haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, Cphd 2-C₆ alkenyl, C₃ -C₆haloalkynyl, C₂ -C₆ alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆nitroalkyl, C₂ -C₆ cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆cycloalkyl, C₃ -C₆ halocycloalkyl, phenyl optionally substituted with 1to 3 substituents independently selected from W, benzyl optionallysubstituted with 1 to 3 substituents independently selected from W,halogen, CN, SCN, NO₂, OR²¹, SR²¹, SO₂ R²¹, CO₂ R²¹, and C(O)R²¹, withone R¹ substituent in the 4-position, or when m is 2 then (R¹)₂ whenattached to adjacent atoms can be taken together as --CH₂ C(CH₃)₂ O--,--OCH₂ CH₂ O--, --OCF₂ CF₂ O--, or --CF₂ CF₂ O-- to form a 5- or6-membered fused ring; R² is selected from the group H, C₁ -C₆ alkyl, C₁-C₆ haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₃-C₆ haloalkynyl, C₂ -C₆ alkoxyalkyl, C₂ -C₆ alkylthioalkyl, C₁ -C₆nitroalkyl, C₂ -C₆ cyanoalkyl, C₃ -C₈ alkoxycarbonylalkyl, C₃ -C₆cycloalkyl, C₃ -C₆ halocycloalkyl, phenyl optionally substituted with 1to 3 substituents independently selected from W, benzyl optionallysubstituted with 1 to 3 substituents independently selected from W,halogen, CN, SCN, NO₂, OR²¹, SR²¹, S(O)₂ R²¹, OC(O)R²¹, OS(O)₂ R²¹, CO₂R²¹, C(O)R²¹, C(O)NR²¹ R²², SO₂ NR²¹ R²² and NR²¹ R²² ; R³ is selectedfrom the group H, C₁ -C₄ alkyl, C₃ -C₄ alkoxycarbonylalkyl, CO₂ R²¹C(O)R²¹, phenyl and phenyl substituted by (R²⁰)p; R²⁰ is selected fromthe group halogen, C₁ -C₂ haloalkyl and CO₂ R²¹ ; R²¹ is selected fromthe group C₁ -C₄ alkyl, C₁ -C₂ haloalkyl, C₃ -C₄ alkenyl and propargyl;R²² is selected from H and CH₃ ; X¹ is selected from the group Cl, OR¹²,SR¹² and N(CH₃)₂ ; X² is selected from the group R¹², OR¹² and N(CH₃)₂ ;m is 1 or 2; n is 1 or 2; and p is 1 or
 2. 3. A compound according toclaim 1 wherein J is selected from the group J-1, J-2, J-8, J-9 andJ-16.
 4. A compound according to claim 2 wherein G is selected from thegroup G-2, G-3, G-7 and G-9.
 5. A compound according to claim 4 whereinAand E are taken together to form --O--, --CH₂ --, --CH₂ CH₂ --, --OCH₂--, --S--, --SCH₂ --, N(R¹¹)CH₂ or NR¹¹ ; R¹¹ is selected from the groupH, C₁ -C₄ alkyl SO₂ R²¹, CO₂ R²¹ and CON(R²¹)R²⁵.
 6. A compoundaccording to claim 5 of Formula I wherein Q is Q-1.
 7. A compoundaccording to claim 5 of Formula I wherein Q is Q-2.
 8. A compoundaccording to claim 5 of Formula II wherein Q is Q-1.
 9. A compoundaccording to claim 5 of Formula II wherein Q is Q-2.
 10. Anarthropodicidal composition comprising an arthropodicidally effectiveamount of a compound according to any one of claims 2 to 5 and 6 to 9and a carrier therefor.
 11. A method for controlling arthropodscomprising applying to them or to their environment an arthropodicidallyeffective amount of a compound according to any one of claims 1 to 2 and6 to 9.